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

HRID 440055Notes

Reaction equation

HRID 440055 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.O.O.Cl[Sn]Cl.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

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 61436Stannous chloride dihydrateHCID 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 SnCl2.2H2O, 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. The pad is washed with ethyl acetate (3×15 ml). The combined ethyl acetate solutions are washed with brine, dried Na2SO4), filtered through hydrous magnesium silicate and evaporated in vacuo to 0.99 g of residue which is stirred with ether-hexanes to give 0.90 g of cream colored solid. MS(CI): 334(M+H).

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
  6. washThe pad is washed with ethyl acetate (3×15 ml)
  7. washThe combined ethyl acetate solutions are washed with brine, dried Na2SO4),
  8. filtrationfiltered through hydrous magnesium silicate
  9. customevaporated in vacuo to 0.99 g of residue which
  10. stirringis stirred with ether-hexanes
  11. customto give 0.90 g of cream

Sources & evidence

ORD record
ord-157c41a772f744f399f56ae96bd36f03
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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