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1-(2-Chloro-4-nitrophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one → 1-(4-Amino-2-chlorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

HRID 442691
ノート
印刷プレビュー

反応式

HRID 442691 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)=[CH:15][C:14]=4[Cl:22])=[N:11][NH:10][C:9](=[O:23])[CH2:8][C:7]=3[CH:24]=[C:3]2[O:2]1.C(O)C.CC(C)=O.O>[Pd].C(O)C>[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)=[C:14]([Cl:22])[CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 540649381-(2-Chloro-4-nitrophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-oneHCID 86654442Ethanol acetone water

生成物 1

HCID 541883761-(4-Amino-2-chlorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one収率 21%

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-(2-chloro-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (1.4 g, 3.9 mmol) in 1:1:1 ethanol/acetone/water (45 mL) was added 5% Pd/C (106 mg) and HCO2NH4 (2.5 g, 40 mmol). The mixture was stirred at room temperature for 3 h and 15 mL of ethanol was added to the mixture which was then stirred at room temperature for three days. The catalyst was filtered out. The filtrate was extracted with EtOAc (100 mL). The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (1:4 hexane/EtOAc) to afford the title compound as a light yellow solid (0.27 g, 0.82 mmol, 21%), mp: 238°-240° C. 1H NMR (CDCl3) 8.34 (s, 1H), 7.41 (d, J=8.6, 1H), 6.81 (s, 1H), 6.69-6.67 (m, 3H), 6.02 (s, 2H), 3.92 (s, 2H), 3.42 (s, 2H).

後処理

  1. stirringwas then stirred at room temperature for three days
  2. filtrationThe catalyst was filtered out
  3. extractionThe filtrate was extracted with EtOAc (100 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (1:4 hexane/EtOAc)

出典と根拠

ORDレコード
ord-e230b17544fb4d00a3bf027f2f01b34a
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05891871

反応ノート

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