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

HRID 1739943Notes

Reaction equation

HRID 1739943 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 1 N 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 1 N 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
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered through hydrous magnesium silicate
  10. customevaporated in vacuo to 0.99 g of residue which
  11. stirringis stirred with ether-hexanes
  12. customto give 0.90 g of cream

Sources & evidence

ORD record
ord-22286890f303497daa2595aff3dead4f
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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