6-Amino-4-butylamino-2-methyl-5-nitronicotinic acid ethyl ester → 5,6-Diamino-4-butylamino-2-methylnicotinic acid ethyl ester

HRID 1973115Notes

Reaction equation

HRID 1973115 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][C:9]([NH2:20])=[C:10]([N+:17]([O-])=O)[C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2]>[Zn].C(O)(=O)C>[NH2:17][C:10]1[C:11]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]([CH3:21])=[N:8][C:9]=1[NH2:20]

Participants

4

Reactant 1

HCID 123876046-Amino-4-butylamino-2-methyl-5-nitronicotinic acid ethyl ester

Product 1

HCID 123876125,6-Diamino-4-butylamino-2-methylnicotinic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

29.6 g. of 6-amino-4-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester are dissolved in 150 ml. of acetic acid. The solution is heated at reflux temperature. Zinc is added carefully until the mixture is colorless (about 20 g.). Heating is continued for an additional 10 minutes. The mixture is then evaporated to dryness and about 100 ml. of water are added. The solution is then neutralized with aqueous ammonia and extracted three times with 100 ml. portions of ether. The ether extracts are combined, dried with calcium chloride and the solvent is evaporated. The oily residue of 5,6-diamino-4-butylamino-2-methylnicotinic acid, ethyl ester crystallizes from methanol, yield: 21 g. (79%), m.p. 82°-83° (methanol/H2O).

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux temperature
  3. temperatureHeating
  4. customThe mixture is then evaporated to dryness and about 100 ml
  5. additionof water are added
  6. extractionextracted three times with 100 ml
  7. dry with materialdried with calcium chloride
  8. customthe solvent is evaporated
  9. customThe oily residue of 5,6-diamino-4-butylamino-2-methylnicotinic acid, ethyl ester crystallizes from methanol, yield: 21 g

Sources & evidence

ORD record
ord-29dfaca6309b4573afe592cc32e89a81
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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