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

HRID 1762805Notes

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

Participants

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

waitto stand at room temperature for 48 hours
filtrationthe green solid (7.16 g) was collected by filtration
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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