Butylamine → 2-Butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester

HRID 27755Notes

Reaction equation

HRID 27755 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.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([NH:20][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)[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 2758816Ethyl 2-chloro-5-cyano-6-methylnicotinate

Product 1

HCID 867372122-Butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester

Procedure

112 g of 2-chloro-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester (0.5 mol) are dissolved in 300 ml of alcohol and 73 g of n-butylamine are dropped in at reflux temperature with stirring. After the addition is completed, the mixture is refluxed for an additional hour and then poured onto ice. 2-butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester precipitates. Yield 116 g (89%); m.p. 61°-63° C. (petrol ether).

Workup

  1. temperatureat reflux temperature
  2. additionAfter the addition
  3. temperaturethe mixture is refluxed for an additional hour
  4. additionpoured onto ice
  5. custom2-butylamino-5-cyano-6-methyl-3-pyridine-carboxylic acid, ethyl ester precipitates

Sources & evidence

ORD record
ord-22bae4bf65454d5684f0495640d96b1c
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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