(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 1632170노트

반응식

HRID 1632170 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 935Nickel촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75da06589c894bfcb93df647a530ff2c
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474777

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