2,3-Diaminonaphthalene → Benzo(g)quinoxalin-2(1H)-one, 3-(3,4-dihydroxy-5-nitrophenyl)-

HRID 274461

반응식

HRID 274461 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:12](=O)[C:13]([O:15]CCCCCC)=O)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[NH2:23][C:24]1[C:33]([NH2:34])=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1>C(O)CCCCC.CO>[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13](=[O:15])[NH:34][C:33]3[CH:32]=[C:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]4=[CH:25][C:24]=3[N:23]=2)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8]

참가 물질

5

반응물 2

HCID 698722,3-DiaminonaphthaleneHCID 5747978Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, hexyl ester

생성물 1

HCID 135624013Benzo(g)quinoxalin-2(1H)-one, 3-(3,4-dihydroxy-5-nitrophenyl)-

시약·촉매·용매 2

HCID 887Methanol용매HCID 81031-Hexanol용매

실험 절차

A solution of 1.07 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 696.3 mg of 2,3-diaminonaphthalene in 3 ml of 1-hexanol is heated to boiling under reflux for 3 hours. The reaction mixture is then cooled and diluted with methanol. The crude product is filtered under suction and recrystallized from N,N-dimethylformamide/water. There is obtained 3-(3,4-dihydroxy-5-nitrophenyl)-benzo[g]quinoxalin-2(1H)-one of m.p. >300°.

후처리

  1. temperatureunder reflux for 3 hours
  2. temperatureThe reaction mixture is then cooled
  3. filtrationThe crude product is filtered under suction
  4. customrecrystallized from N,N-dimethylformamide/water

출처 및 근거

ORD 기록
ord-fde2b8f971464dcc93763b04fea1b822
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389653

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