(S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one → (S)-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

HRID 1632170ノート

反応式

HRID 1632170 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[N:12]([CH3:22])[C:11](=[O:23])[C@H:10]([CH3:24])[N:9]=1>O1CCCC1.CO.[Ni]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:22])[C:11](=[O:23])[C@H:10]([CH3:24])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1

参加物

5

反応物 1

HCID 54101851(S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

生成物 1

HCID 54176638(S)-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 68.2 g (0.198 mol) of (S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one in a mixture of 400 ml of tetrahydrofuran and 950 ml of methanol is treated with Raney-nickel which has previously been washed several times with methanol and tetrahydrofuran and the suspension is hydrogenated while stirring and cooling with water, whereupon it is filtered and the filtrate is evaporated. The residue is recrystallized from ether, there being obtained (S)-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one of melting point 221°; [α]25D =-13.8° (1 percent solution in methylene chloride).

後処理

  1. washhas previously been washed several times with methanol and tetrahydrofuran
  2. temperaturecooling with water, whereupon it
  3. filtrationis filtered
  4. customthe filtrate is evaporated
  5. customThe residue is recrystallized from ether, there

出典と根拠

ORDレコード
ord-75da06589c894bfcb93df647a530ff2c
出典データセット
uspto-grants-1984_10
特許番号
US04474777

反応ノート

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