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

HRID 442690

반응식

HRID 442690 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f1154808b6284b6db594b7354be3e143
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891871

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