Sodium Hydroxide → 1-(2-Methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729084Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1.P(N)([NH2:34])(=O)OC1C=CC=CC=1.[OH-].[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[N:14]=[C:13]([NH2:34])[C:12]=2[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 230 °C

Procedure

1-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (1.5 g) and phenyl phosphorodiamidate (2.5 g) were fused at 230° C. After 45 minutes the mixture was diluted with diphenyl ether (10 ml), further phenyl phosphorodiamidate (2 g) added, and heated for a further 15minutes at 230° C. Aqueous sodium hydroxide was added and the product extracted into dichloromethane. Chromatography (silica gel. 2.5-4%methanolic ammonia in dichloromethane) to remove unchanged starting material was followed by recrystallisation from ethanol/ethyl acetate to yield 1-(2-methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline (0.36 g), m.p. 244°-247° (dec).

Workup

customwere fused at 230° C
additionadded
extractionthe product extracted into dichloromethane
customChromatography (silica gel. 2.5-4%methanolic ammonia in dichloromethane) to remove unchanged
customwas followed by recrystallisation from ethanol/ethyl acetate

Sources & evidence

ORD record: ord-cdad40774a3b4704af12b9b0a2d3f3f8
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051508

Reaction notes

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