Acetic Anhydride → 5,14-Dihydro-7-methylbenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione

HRID 1762808노트

반응식

HRID 1762808 반응식
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12](O)=O)[NH:3]1.[C:15]1(=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[CH:17]=[CH:16]1.[C:27](OC(=O)C)(=O)C>>[CH3:27][C:16]1[N:3]2[CH2:2][C:11]3[C:6]([CH2:5][C:4]2=[C:12]2[C:17]=1[C:18](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[C:15]2=[O:26])=[CH:7][CH:8]=[CH:9][CH:10]=3

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 85301,4-NaphthoquinoneHCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

생성물 1

HCID 200397275,14-Dihydro-7-methylbenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione

반응 조건

온도
100 °C

실험 절차

A mixture of 1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid hydrochloride (4.0 g) and 1,4-naphthoquinone (5.5 g) in acetic anhydride (115 ml) was heated at 100° C. with stirring for 5.5 hours. The reaction mixture was cooled and the green crystalline solid was collected by filtration, washed with acetic anhydride and ether and dried. Recrystallisation from acetic anhydride afforded the title compound (3.5 g), decomposes 240°-245° C. (cap.) without loss of crystalline form λmax (in ethanol) 245 (ε60,470), 265.5 (ε15,270) and 386 nm (ε7706).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe green crystalline solid was collected by filtration
  3. washwashed with acetic anhydride and ether
  4. customdried
  5. customRecrystallisation from acetic anhydride

출처 및 근거

ORD 기록
ord-b00a817c3405470cb6ad58123cfd598d
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04835158

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