Hydrazine hydrate (1:1) → HCID 9840673, compound

HRID 1292029Notes

Reaction equation

HRID 1292029 reaction equation
O.NN.[C:4]([N:7]1[C:13]([CH3:14])=[CH:12][C:11]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:10]=2[C:9]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[N:8]1)(=[O:6])[CH3:5]>[Ni].CO>[C:4]([N:7]1[C:13]([CH3:14])=[CH:12][C:11]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:10]=2[C:9]([C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=2)=[N:8]1)(=[O:6])[CH3:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15299309HCID 15299309, compound

Product 1

HCID 9840673HCID 9840673, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

0.1 g of Raney nickel and 0.25 ml (4.93 mmol) of 98% hydrazine hydrate are added to a suspension of 0.6 g (1.64 mmol) of 7-acetyl-5-(4-nitrophenyl)-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine in 40 ml of methanol. The mixture is stirred for 0.5 hour. The starting material is dissolved within a few minutes. After the reaction is completed, catalyst is filtered out. The filtrate is concentrated by evaporation in a vacuum. The residue is absorptively precipitated in water, suctioned off and rewashed with water. 0.49 g of 7-acetyl-5-(4-aminophenyl)-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine with a melting point of 175°-180° C. is obtained. Recrystallization of this crude product from 50% aqueous ethanol yields 0.46 g (79%) of 7-acetyl-5-(4-amino-phenyl)-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine with a melting point of 208°-210° C.

Workup

  1. dissolutionThe starting material is dissolved within a few minutes
  2. filtrationcatalyst is filtered out
  3. concentrationThe filtrate is concentrated by evaporation in a vacuum
  4. customThe residue is absorptively precipitated in water

Sources & evidence

ORD record
ord-17d4fa43bb3e401c9f16cb221020af41
Source dataset
uspto-grants-1998_05
Patent number
US05756495

Reaction notes

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