Hydrochloric Acid → HCID 9839097、化合物

HRID 442669ノート

反応式

HRID 442669 の反応式
[CH2:1]1[O:24][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][CH:14]=4)=[N:11][NH:10][C:9](=[O:22])[CH2:8][C:7]=3[CH:23]=[C:3]2[O:2]1.O.NN.Cl>C(O)C.[Ni]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:6]3[CH:5]=[C:4]4[O:24][CH2:1][O:2][C:3]4=[CH:23][C:7]=3[CH2:8][C:9](=[O:22])[NH:10][N:11]=2)=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 10829879HCID 10829879、化合物

生成物 1

HCID 9839097HCID 9839097、化合物収率 73%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

To a suspension of 7,8-methylenedioxy-1-(4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (167 mg, 0.51 mmol) in ethanol (8 mL) was added Raney Ni (430 mg), hydrazine hydrate (200 μL, 3.5 mmol) and 2N HCl (150 μL, 0.3 mmol). The mixture was stirred at room temperature for 17 h. The solid Ni was filtered out. The filtrate was concentrated in vacuo and the resulting residue was separated by chromatography (1:4 hexane/EtOAc) to afford the title compound as a yellow solid (110 mg, 0.37 mmol, 73%), mp: 242°-244° C. 1H NMR (CDCl3) 8.32 (s, 1H), 7.41 (d, 2H, J=8.5), 6.81 (s, 1H), 6.70 (s, 1H), 6.68 (d, 2H, J=8.5), 6.02 (s, 2H), 3.94 (brs, 2H), 3.42 (s, 2H). Anal. Calcd. for C16H13N3O3.0.25H2O: C, 64.10; H, 4.54; N, 14.02. Found C, 64.32; H, 4.37; N, 13.48.

後処理

  1. filtrationThe solid Ni was filtered out
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was separated by chromatography (1:4 hexane/EtOAc)

出典と根拠

ORDレコード
ord-45442c3b60da4c3d8dad49574172205d
出典データセット
uspto-grants-1999_04
特許番号
US05891871

反応ノート

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