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1,4-Naphthoquinone → 5,14-Dihydro-7-phenylbenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione

HRID 1762805
Notes
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Reaction equation

HRID 1762805 reaction equation
[C:1]([N:9]1[CH:18](C(O)=O)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1(=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[CH:24]=[CH:23]1>C(OC(=O)C)(=O)C>[C:2]1([C:1]2[N:9]3[CH2:10][C:11]4[C:16]([CH2:17][C:18]3=[C:23]3[C:24]=2[C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:22]3=[O:33])=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 5700052-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 200397325,14-Dihydro-7-phenylbenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dioneYield 62.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-benzoyl-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (6.0 g) and 1,4-naphthalenedione (6.75 g) in acetic anhydride (240 ml) was stirred at about 100° C. for 20 minutes. The reaction mixture was allowed to stand at room temperature for 48 hours, and the green solid (7.16 g) was collected by filtration. The crude product was recrystallised from chloroform-petroleum ether (b.b. 40°-60° C.) to give the title compound (5.04 g) m.p. 267° C. (decomp), λmax (in ethanol) 246.5 nm (ε45,500), 320 nm (ε2,440), 388 nm (ε6,120).

Workup

  1. waitto stand at room temperature for 48 hours
  2. filtrationthe green solid (7.16 g) was collected by filtration
  3. customThe crude product was recrystallised from chloroform-petroleum ether (b.b. 40°-60° C.)

Sources & evidence

ORD record
ord-8c87b84164384f80b6c289017c7acae7
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04835158

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes