4-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester → HCID 178448823, compound

HRID 1606537Notes

Reaction equation

HRID 1606537 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][C:9](Cl)=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2].O.[S-2:23].[Na+].[Na+]>O>[CH2:13]([NH:12][C:11]1[C:10]([N+:17]([O-:19])=[O:18])=[C:9]([SH:23])[N:8]=[C:7]([CH3:21])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 123875984-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl esterHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 178448823HCID 178448823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

31.5 g. of 4-butylamino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.1 Mol.) are dissolved in 100 ml. of alcohol. 14.8 g. of sodium sulfide monohydrate and about 2 ml. of water are added and the mixture is stirred for one hour without cooling. The precipitated 4-butylamino-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester is filtered off, yield 27.5 g. (88%), m.p. 140°-142° (ethanol).

Workup

  1. temperaturewithout cooling
  2. filtrationThe precipitated 4-butylamino-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester is filtered off

Sources & evidence

ORD record
ord-7c80a20332fd47da867596a1aa962b71
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

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