HCID 178448823, compound → HCID 178448828, compound

HRID 1606538Notes

Reaction equation

HRID 1606538 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[C:10]([SH:15])[N:9]=[C:8]([CH3:16])[C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:2][CH2:3][CH3:4]>[Zn].C(O)(=O)C>[NH2:12][C:11]1[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]([CH3:16])=[N:9][C:10]=1[SH:15]

Participants

4

Reactant 1

HCID 178448823HCID 178448823, compound

Product 1

HCID 178448828HCID 178448828, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

6.2 g. of 4-butylamino-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester (0.02 Mol.) are dissolved in 25 ml. of acetic acid at reflux temperature with stirring. Zinc dust is added cautiously in small portions until the solvent is colorless. The inorganic precipitate is then filtered off, the solvent is removed and the residue is dissolved in 10 ml. of methanol. The product 5-amino-4-butylamino-6-mercapto-2-methylpyridine-3-carboxylic acid, ethyl ester precipitates after the addition of aqueous ammonia, yield 3.6 g. (64%), m.p. 103°-105° (ethyl acetate).

Workup

  1. filtrationThe inorganic precipitate is then filtered off
  2. customthe solvent is removed
  3. dissolutionthe residue is dissolved in 10 ml
  4. customThe product 5-amino-4-butylamino-6-mercapto-2-methylpyridine-3-carboxylic acid, ethyl ester precipitates
  5. additionafter the addition of aqueous ammonia, yield 3.6 g

Sources & evidence

ORD record
ord-96bbccaf875d403ba8c3e47e349107e3
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

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