HCID 178469258, compound → HCID 178469256, compound

HRID 1658524Notes

Reaction equation

HRID 1658524 reaction equation
[CH: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])([CH2:3][CH3:4])[CH3:2]>[Fe].C(O)(=O)C>[NH2:12][C:11]1[C:6]([NH:5][CH:1]([CH2:3][CH3:4])[CH3:2])=[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 178469258HCID 178469258, compound

Product 1

HCID 178469256HCID 178469256, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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 reflux temperature until the mixture is colorless. The excess of 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. temperatureat reflux temperature until the mixture
  2. filtrationThe excess of 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-5b50792b90814ca795934a83d214c8ce
Source dataset
uspto-grants-1976_06
Patent number
US03965108

Reaction notes

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