3-Methoxyimino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione → 3-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

HRID 1955591Notes

Reaction equation

HRID 1955591 reaction equation
CO[N:3]=[C:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[NH:6][C:5]1=[O:16]>CO.[Pd]>[NH2:3][CH:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[NH:6][C:5]1=[O:16]

Participants

4

Reactant 1

HCID 190708143-Methoxyimino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dioneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-methoxyimino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione (3.78 g, 17.4 mmol) and 10% Pd/C (1.8 g) in methanol (300 ml) is stirred for 15 hr under hydrogen gas. After removing the catalyst by filtration, the filtrate is concentrated under reduced pressure. The resultant residue is crystallized from methanol to obtain Compound 4 (2.062 g, 62%). M.p. =290°-291° C.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe resultant residue is crystallized from methanol

Sources & evidence

ORD record
ord-3750335c39af421c8408009500338618
Source dataset
uspto-grants-1998_07
Patent number
US05776929

Reaction notes

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