Acetic Acid → HCID 178469256, compound

HRID 1606541Notes

Reaction equation

HRID 1606541 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]C.[C:22](O)(=O)C>[Fe]>[NH2:12][C:11]1[C:6]([NH:5][CH:1]([CH2:2][CH3:3])[CH3:22])=[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 2

HCID 176Acetic AcidHCID 178448823HCID 178448823, compound

Product 1

HCID 178469256HCID 178469256, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

6.2 g. of 4-sec. butylamino-6-mercapto-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester are dissolved in 50 ml. of acetic acid. Iron dust is added carefully at relufx temperature until the mixture is colorless. The excess iron is filtered off and the filtrate is evaporated to dryness. The oily residue is dissolved in 10 ml. of methanol and precipitated by the addition of aqueous ammonia to obtain 5-amino-4-sec.butylamino-6-mercapto-2-methylpyridine-3-carboxylic acid, ethyl ester, yield 3 g. (53%), m. p. 88°-89° (ethyl acetate).

Workup

  1. waitof 4-sec
  2. filtrationThe excess iron is filtered off
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe oily residue is dissolved in 10 ml
  5. customof methanol and precipitated by the addition of aqueous ammonia

Sources & evidence

ORD record
ord-15e59bded2404e17bdf140062c9e5a41
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

Loading…