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

HRID 1762808Notes

Reaction equation

HRID 1762808 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b00a817c3405470cb6ad58123cfd598d
Source dataset
uspto-grants-1989_05
Patent number
US04835158

Reaction notes

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