Ethanol → 2-hydrazino-5-phenyl-3H-1,4-benzodiazepine

HRID 1764502Notes

Reaction equation

HRID 1764502 reaction equation
[NH2:1][C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.C(O)C.O.[NH2:23]N>C(O)(=O)C>[NH:1]([C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1)[NH2:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 125695872-amino-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 126123892-hydrazino-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2.35 parts of 2-amino-5-phenyl-3H-1,4-benzodiazepine, 50 parts by volume of ethanol and 1.2 parts by volume of glacial acetic acid is added 1.5 parts by volume of 100% hydrazine hydrate and the mixture is stirred for 1 hour at room temperature. Treatment of the mixture in a similar manner to Example 2 yields 2-hydrazino-5-phenyl-3H-1,4-benzodiazepine as white crystals. Recrystallization from a mixture of methylene chloride and benzene yields white crystals melting at 116° to 118° C. (effervescence).

Sources & evidence

ORD record
ord-44ac2a2a38ee4f3f895c24e463fb5da4
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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