HCID 178448823, compound → HCID 178448828, compound

HRID 1658523Notes

Reaction equation

HRID 1658523 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 preceipitate is then filtered off, the solvent removed and the residue 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 preceipitate is then filtered off
  2. customthe solvent removed
  3. dissolutionthe residue 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-5deba5309fdd4ca3affaa13a7164e2e2
Source dataset
uspto-grants-1976_06
Patent number
US03965108

Reaction notes

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