Methyl formate → HCID 23367277, compound

HRID 1080365Notes

Reaction equation

HRID 1080365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH3:10][O:11]C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH:10]=[O:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7865Methyl formateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 23367277HCID 23367277, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 g of 91.7% pure (0.1 mol) 2-chloro-5-cyanopyridine were hydrogenated in a mixture of 70 ml of methylformate and 50 ml of toluene analogously to Example 1. After analysis by gas chromatography, 2-chloro-5-(formylaminomethyl)pyridine had formed in a yield of 86.7% of theory. 2-Chloro-5-(aminomethyl)pyridine (3.6% of theory) and di(2-chloro-5-methylpyridyl)amine (2.0% of theory) were identified as by-products. The crude product was boiled under reflux with 30 ml of 20% strength NaOH for 2 hours. After extraction with CH2Cl2 and concentration, the residue was distilled in vacuo. 12 g of 98.7% pure goods, corresponding to 83.1% of theory, based on the 2-chloro-5-cyanopyridine, were obtained.

Sources & evidence

ORD record
ord-7c0466a3132f41db843b6841575149f6
Source dataset
uspto-grants-1996_12
Patent number
US05580983

Reaction notes

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