Water → 1-(4-Amino-3-methylphenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

HRID 442690Notes

Reaction equation

HRID 442690 reaction equation
[CH2:1]1[O:25][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]([CH3:22])[CH:14]=4)=[N:11][NH:10][C:9](=[O:23])[CH2:8][C:7]=3[CH:24]=[C:3]2[O:2]1.O>C(O)C.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:6]3[CH:5]=[C:4]4[O:25][CH2:1][O:2][C:3]4=[CH:24][C:7]=3[CH2:8][C:9](=[O:23])[NH:10][N:11]=2)=[CH:14][C:15]=1[CH3:22]

Participants

5

Reactant 2

HCID 962WaterHCID 538477727,8-Methylenedioxy-1-(3-methyl-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

Product 1

HCID 444527031-(4-Amino-3-methylphenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-oneYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 7,8-methylenedioxy-1-(3-methyl-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (147 mg, 0.433 mmol) in ethanol (5 mL) was added water (2.5 mL), 5% Pd/C (42 mg), and HCO2NH4 (320 mg, 5.07 mmol). The mixture was stirred at room temperature for 4 h. The catalyst was filtered out. The filtrate was concentrated in vacuo and water (25 mL) was then added to the residue. The resulting solid was collected by filtration, washed with water, and dried in vacuo to afford the title compound as a light yellow solid (65 mg, 0.21 mmol, 49%), mp: 164°-166° C. 1H NMR (CDCl3) 8.23 (s, 1H), 7.35-7.22 (m, 2H), 6.82 (s, 1H), 6.71-6.65 (m, 2H), 6.03 (s, 2H), 3.87 (s, 2H), 3.42 (s, 2H), 2.19 (s, 2H). Anal. calcd. for C17H15N3O3.H2O: C, 62.38; H, 5.23; N, 12.84. Found: C, 62.50; H, 5.19; N, 12.86.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationThe filtrate was concentrated in vacuo and water (25 mL)
  3. additionwas then added to the residue
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f1154808b6284b6db594b7354be3e143
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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