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

HRID 442690

反応式

HRID 442690 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f1154808b6284b6db594b7354be3e143
出典データセット
uspto-grants-1999_04
特許番号
US05891871

関連ノート

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