Naphthazarin diacetate → HCID 20039729, compound

HRID 1762807Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][C:16](=[O:18])[CH3:17])=[C:11]2[C:6]=1[C:7](=[O:20])[CH:8]=[CH:9][C:10]2=[O:19])(=[O:3])[CH3:2].[CH:21]([N:23]1[CH:32](C(O)=O)[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=O>C(OC(=O)C)(=O)C>[C:16]([O:15][C:12]1[C:11]2[C:10](=[O:19])[C:9]3[C:8]([C:7](=[O:20])[C:6]=2[C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=1)=[C:32]1[N:23]([CH2:24][C:25]2[C:30]([CH2:31]1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=3)(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 20 °C

Procedure

5,8-bis(acetyloxy)-1,4-napthalenedione (4.28 g) and 2-formyl-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (1.60 g) in acetic anhydride (65 ml) were heated at 100° C. (20 minutes). The reaction mixture was cooled at about 20° C. (1 h), and the solid was collected by filtration, washed with ether (3×30 ml) and dried in vacuo. The crude product was dissolved in dichloromethane and the solution was loaded onto a column of silica gel (175 g) packed in dichloromethane. The column was eluted with 5% (v/v) ethyl acetate in dichloromethane and fractions containing the major component were evaporated to dryness, and further dried in vacuo at 55° C. to give the title compound as a yellow-green solid (1.34 g), m.p. 228°-232° C. (dec), λmax (in CH2Cl2) 242 nm (ε40,700), 377 nm (ε6,400).

Workup

filtrationthe solid was collected by filtration
washwashed with ether (3×30 ml)
customdried in vacuo
dissolutionThe crude product was dissolved in dichloromethane
washThe column was eluted with 5% (v/v) ethyl acetate in dichloromethane and fractions
additioncontaining the major component
customwere evaporated to dryness
customfurther dried in vacuo at 55° C.

Sources & evidence

ORD record: ord-01cfc379a9434596b41ddf612a4d7893
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835158

Reaction notes

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