O-Toluidine → HCID 20529026, compound

HRID 66774

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH2:19][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>O1CCCC1>[ClH:1].[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]2[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5.31 g (19.98 mmoles) of ethyl 4-chloro-8-methoxy-3-quinolinecarboxylate dissolved in 40 ml of tetrahydrofuran was added 2.15 g (20.06 mmoles) of o-toluidine dissolved in 40 ml of tetrahydrofuran. The solution was stirred with exclusion of moisture at 60° C. for 18 hours. The yellow solid precipitate was filtered and washed with isopropyl ether; yield 7.13 g (95.7%). The product was recrystallized three times from methylene chloride: ethyl acetate, m.p. 191°-193.5° C.

Workup

filtrationThe yellow solid precipitate was filtered
washwashed with isopropyl ether
customThe product was recrystallized three times from methylene chloride

Sources & evidence

ORD record: ord-97812384425e455ea7ccbb58d5853e9b
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04343804

Linked notes

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