HCID 67895874, compound → HCID 67896068, compound

HRID 2073236Notes

Reaction equation

HRID 2073236 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13](=[O:15])[CH3:14])[NH2:12])=[C:7]([N+:16]([O-])=O)[CH:6]=1)=[O:4].[H][H]>[Pd].COC(O)C>[NH2:16][C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=[CH:9][C:8]=1[N:11]([C:13](=[O:15])[CH3:14])[NH2:12]

Participants

5

Reactant 2

HCID 67895874HCID 67895874, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67896068HCID 67896068, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 30156371-MethoxyethanolSolvent

Procedure

2.5 g of 10% palladium-on-carbon catalyst were added to a solution of 25.3 g of 4-methoxycarbonyl-2-nitro-N-acetylphenylhydrazine in 380 ml of methoxyethanol and the mixture was hydrogenated in a shaking equipment until the hydrogen uptake ceased. After filtering off the catalyst, the filtrate was evaporated under reduced pressure and the residue was mixed with 100 ml of water. The separated crystals were filtered by suction, washed with water and dried at 80° C. Thus, 19.1 g (85.6%) of 2-amino-4-methoxycarbonyl-N-acetylphenylhydrazine were obtained as a beige crystalline solid, m.p.: 175°-178° C. After recrystallization from methanol, the m.p. was raised to 180°-182° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe filtrate was evaporated under reduced pressure
  3. additionthe residue was mixed with 100 ml of water
  4. filtrationThe separated crystals were filtered by suction
  5. washwashed with water
  6. customdried at 80° C

Sources & evidence

ORD record
ord-a0eb2fe6ef2449b8b12a288c0081562a
Source dataset
uspto-grants-1990_04
Patent number
US04916149

Reaction notes

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