Ethanol → (4-amino-3-methoxy-phenyl)[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl]methanone

HRID 1740057Notes

Reaction equation

HRID 1740057 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][C:5]=1[O:26][CH3:27])([O-])=O.C(O)C.O1CCCC1>C(Cl)Cl>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][C:5]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 1071374010,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 10806563(4-amino-3-methoxy-phenyl)[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.91 g of 10,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 4.51 g of SnCl 2.2H2O, 6 ml of ethyl alcohol, 6 ml of tetrahydrofuran and 16 ml of methylene chloride is stirred at 50° C. for 2 hours. The solvents are evaporated in vacuo and the residue dissolved in 80 ml of ethyl acetate. The solution is treated with 50 ml of 1N NaOH with stirring for 30 minutes. The resulting suspension is filtered through diatomaceous earth.

Workup

  1. customThe solvents are evaporated in vacuo
  2. dissolutionthe residue dissolved in 80 ml of ethyl acetate
  3. additionThe solution is treated with 50 ml of 1N NaOH
  4. stirringwith stirring for 30 minutes
  5. filtrationThe resulting suspension is filtered through diatomaceous earth

Sources & evidence

ORD record
ord-92d9e5f99d1a4924b00d4c7580e1ef5c
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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