Methanol → HCID 22768408, compound

HRID 1764501Notes

Reaction equation

HRID 1764501 reaction equation
[NH2:1][C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:4]=2[N:3]=1.CO.O.[NH2:25]N>C(O)(=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:4]2[N:3]=[C:2]([NH:1][NH2:25])[CH2:8][N:7]=[C:6]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[C:5]=2[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 12569589HCID 12569589, compound

Product 1

HCID 22768408HCID 22768408, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3 parts of 2-amino-7-chloro-5-(p-methoxyphenyl)-3H-1,4-benzodiazepine in a mixture of 50 parts by volume of methanol and 0.6 part by volume of glacial acetic acid is added dropwise with stirring 1.5 parts by volume of 100% hydrazine hydrate. The mixture is stirred for 30 minutes and poured into ice water, followed by extraction with chloroform. The chloroform layer is washed with water, dried over sodium sulfate and the solvent is evaporated. Treatment of the residue with benzene yields 7-chloro-2-hydrazino-5-(p-methoxypheyl)-3H-1,4-benzodiazepine as colorless crystals melting at 214° C to 220° C.

Workup

  1. additionis added dropwise
  2. extractionfollowed by extraction with chloroform
  3. washThe chloroform layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-80046da8c6ab419285444cf51c99dc8f
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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