Water → 5-Cyano-6-methyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester

HRID 27762

Reaction equation

HRID 27762 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([C:13]#[N:14])=[C:4]([CH3:15])[N:3]=1.[CH:16]([NH2:20])([CH2:18][CH3:19])[CH3:17].O>C(O)C>[C:13]([C:5]1[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]([NH:20][CH:16]([CH3:17])[CH2:18][CH3:19])=[N:3][C:4]=1[CH3:15])#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24874Sec-ButylamineHCID 2758816Ethyl 2-chloro-5-cyano-6-methylnicotinate

Product 1

HCID 867372195-Cyano-6-methyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

22.4 g of 2-chloro-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester (1 mol) of Example 1(b) are treated in 100 ml of ethanol with 15 g sec. butylamine at reflux temperature with stirring. After the addition of the amine is completed, the solution is poured into 200 ml of cold water, and the amino compound is filtered off. Yield 22 g (84%); m.p. 55°-57° C.

Workup

  1. temperatureat reflux temperature
  2. filtrationthe amino compound is filtered off

Sources & evidence

ORD record
ord-8ae000ca848e414ea1ff080f0b71df04
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Linked notes

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