Ethanol → HCID 44452705, compound

HRID 442689Notes

Reaction equation

HRID 442689 reaction equation
[CH2:1]1[O:26][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([O:22][CH3:23])[CH:14]=4)=[N:11][NH:10][C:9](=[O:24])[CH2:8][C:7]=3[CH:25]=[C:3]2[O:2]1.C(O)C.O>CC(C)=O.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:6]3[CH:5]=[C:4]4[O:26][CH2:1][O:2][C:3]4=[CH:25][C:7]=3[CH2:8][C:9](=[O:24])[NH:10][N:11]=2)=[CH:14][C:15]=1[O:22][CH3:23]

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 53646949HCID 53646949, compound

Product 1

HCID 44452705HCID 44452705, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 7,8-methylenedioxy-1-(3-methoxy-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (136 mg, 0.387 mmol) in acetone (6 mL) was added ethanol (3 mL), water (4 mL), 5% Pd/C (33 mg) and HCO2NH4 (240 mg, 3.81 mmol). The mixture was stirred at room temperature for 3 h. The catalyst was filtered out. The filtrate was concentrated in vacuo and the resulting residue was collected by filtration, washed with water, and dried in vacuo to afford the title compound as a light yellow solid (98 mg, 0.31 mmol, 80%), mp: 147°-150° C. 1H NMR (CDCl3) 8.32 (s, 1H), 7.24 (d, J=1.9, 1H), 6.87 (dd, J=1.9, 8.0, 1H), 6.82 (s, 1H), 6.73 (s, 1H), 6.02 (s, 2H), 4.08 (s, 2H), 3.90 (s, 3H), 3.43 (s, 211). Anal. calcd. for C17H15N3O4.(3/8)H2O: C, 61.49; H, 4.78; N, 12.65. Found: C, 61.33; H, 4.39; N, 12.54.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationThe filtrate was concentrated in vacuo
  3. filtrationthe resulting residue was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-71ed8322417b4032a3d1690d8ecc9cbe
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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