Production Method 1

92444-89-8

92444-99-0

Reaction Conditions

Reference

High-yield process for the preparation of 2-chloro-5-methylpyridine-3-carbaldehyde from the reaction of DMF and N-benzyl-N-(1-propenyl)acetamide with diphosgene or triphosgene

, United States, , ,

Production Method 2

92444-89-8

92444-99-0

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  30 min, 0 °C
1.2 0 °C; 2 h, 25 °C; 5 h, 25 °C → 75 °C
1.3 Solvents: Water

Reference

Process for the preparation of 2-chloro-5-methylpyridine-3-carboxaldehyde via the reaction of N-benzyl-N-(1-propenyl)acetamide with a Vilsmeier reagent

, United States, , ,

Production Method 3

92444-99-0

Reaction Conditions

Reference

Process for the preparation of 2-halopyridinealdehydes from substituted olefins in the presence of Vilsmeyer reagents

, Germany, , ,

Production Method 4

92444-99-0

Reaction Conditions

Reference

A versatile new synthesis of quinolines and related fused pyridines. Part 12. A general synthesis of 2-chloropyridines and 2-pyridones

Meth-Cohn, Otto; Westwood, Keith T., Journal of the Chemical Society, 1984, (6), 1173-82

Production Method 5

159117-50-7

92444-99-0

92444-98-9

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of non-aromatic compounds

Jones, Gurnos; Stanforth, Stephen P., Organic Reactions (Hoboken, 2000, 56,

Production Method 6

159117-50-7

92444-99-0

Reaction Conditions

1.1 Reagents: Diphosgene ;  30 min, 0 °C
1.2 0 °C; 2 h, rt; rt → 75 °C; 5 h, 75 °C

Reference

Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Gangadasu, B.; Narender, P.; Kumar, S. Bharath; Ravinder, M.; Rao, B. Ananda; et al, Tetrahedron, 2006, 62(35), 8398-8403

Production Method 7

92444-89-8

92444-99-0

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  30 min, 4 °C
1.2 4 °C; 2 h, 25 °C; 5 h, 25 °C → 75 °C

Reference

A process for the preparation of 2-chloro-5-methylpyridine-3-carbaldehyde

, India, , ,

Production Method 8

18368-64-4

92444-99-0

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  1 h, 15 - 25 °C; 0.5 h, 15 - 25 °C
1.2 Solvents: 1,2-Dichloroethane ;  0.5 h, 15 - 25 °C; 2 h, 20 - 25 °C; 25 °C → 88 °C; 5 h, 88 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 11, 25 - 30 °C
1.4 Reagents: Water ;  100 °C

Reference

Preparation of 2-chloro-5-methylpyridine-3-carbaldehyde

, China, , ,

Production Method 9

100368-56-7

92444-99-0

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  30 min, 0 °C
1.2 0 °C; 2 h, rt; 4 h, 70 °C
1.3 Reagents: Water ;  cooled

Reference

Preparation of heteroaryls as inhibitors of dipeptidyl peptidase

, China, , ,

Production Method 10

92444-89-8

92444-99-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Dimethylformamide ;  30 min, 0 °C
1.2 0 °C; 2 h, 25 °C; 5 h, 25 °C → 75 °C

Reference

An improved method for the preparation of 2-chloro-5-methylpyridine-3-carbaldehyde

, India, , ,

Production Method 11

109-94-4

18368-64-4

92444-99-0

Reaction Conditions

1.1 Reagents: Butyllithium ,  2,2,6,6-Tetramethylpiperidine Solvents: Tetrahydrofuran ;  -78 °C; -78 °C → 0 °C; 20 min, 0 °C; 0 °C → -78 °C
1.2 5 min, -78 °C; 2.5 h, -78 °C
1.3 -78 °C; 30 min, -78 °C → -40 °C
1.4 Reagents: Water Solvents: Tetrahydrofuran ;  -40 °C

Reference

Site-selective γ-C(sp3)-H and γ-C(sp2)-H arylation of free amino esters promoted by a catalytic transient directing group

Lin, Hua ; Wang, Chao; Bannister, Thomas D.; Kamenecka, Theodore M., Chemistry - A European Journal, 2018, 24(38), 9535-9541

Production Method 12

92444-89-8

92444-99-0

Reaction Conditions

Reference

Synthesis and in vitro antitumor activity of new nicotinyl-rhodanine derivatives

Rao, Boddu Ananda; Rajpoot, Ravindra Singh; Naidu, V. G. M.; Srinivas, Kolupula; Ramakrishna, Sistla; et al, International Journal of Pharma and Bio Sciences, 2011, 2(4), 191-202

Production Method 13

159117-50-7

92444-99-0

Reaction Conditions

1.1 Reagents: Phosgene Solvents: Dimethylformamide ;  30 min, 0 °C; 2 h, rt; 4.5 h, rt → 75 °C

Reference

Preparation of heteroaryl antagonists of prostaglandin D2 receptors for therapy

, World Intellectual Property Organization, , ,

2-Chloro-5-methylpyridine-3-carbaldehyde Raw materials

• Ethyl formate
• (E)-n-benzyl-n-(prop-1-enyl)acetamide
• N-Benzyl-N-[(E)-prop-1-enyl]acetamide
• 2-Chloro-5-methylpyridine
• N-Propyl-N-benzyl-acetamid

2-Chloro-5-methylpyridine-3-carbaldehyde Preparation Products

• 2-Chloro-5-methylpyridine-3-carbaldehyde (92444-99-0)
• 2(1H)-Pyridinone, 5-methyl-1-(phenylmethyl)- (92444-98-9)

• 1. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 2. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 3. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 4. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 5. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridine carboxaldehydes

• 36404-88-3(2-Chloronicotinaldehyde)
• 176433-43-5(6-chloro-5-methyl-pyridine-3-carbaldehyde)
• 176433-49-1(2,5-Dichloronicotinaldehyde)
• 176433-57-1(3-Pyridinecarboxaldehyde,2-chloro-5-phenyl-)
• 73568-27-1(2-Chloro-6-methylquinoline-3-carbaldehyde)
• 73568-41-9(2,6-Dichloroquinoline-3-carbaldehyde)
• 134031-24-6(2,4-dichloropyridine-3-carbaldehyde)
• 55304-73-9(2,6-Dichloropyridine-3-carbaldehyde)
• 23100-12-1(6-chloropyridine-3-carbaldehyde)
• 73568-25-9(2-Chloroquinoline-3-carbaldehyde)