Hydrazine → 10,11-Dihydro-10-(4-amino-3-methylbenzoyl)-5H-Pyrrolo[2,1-c][1,4]benzodiazepine

HRID 439964Notes

Reaction equation

HRID 439964 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[N+:24]([O-])=O)[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][N:10]2[CH:18]=[CH:19][CH:20]=[C:9]2[CH2:8]1)=[O:6].NN>C(O)C.[Pd]>[NH2:24][C:23]1[CH:22]=[CH:21][C:4]([C:5]([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][N:10]3[CH:18]=[CH:19][CH:20]=[C:9]3[CH2:8]2)=[O:6])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 1052158310,11-dihydro-10-(3-methyl-4-nitro-benzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1068697510,11-Dihydro-10-(4-amino-3-methylbenzoyl)-5H-Pyrrolo[2,1-c][1,4]benzodiazepineYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.22 g 10,11-dihydro-10-(3-methyl-4-nitro-benzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.2 g of 10% Pd/C and 0.35 g of anhydrous hydrazine in 50 ml of absolute ethyl alcohol is heated on a steam bath for 1 hour. The reaction mixture is filtered hot through diatomaceous earth and evaporated in vacuo to a residue. The residue is crystallized from methylene chloride-hexane to give 0.95 g of the desired product as crystals, m.p. 232°-234° C.

Workup

  1. temperatureis heated on a steam bath for 1 hour
  2. filtrationThe reaction mixture is filtered hot through diatomaceous earth
  3. customevaporated in vacuo to a residue
  4. customThe residue is crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-a7d22a3c81b64154ae7c8fc14a3dee2e
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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