4-Chloroquinoline → HCID 18326772, compound

HRID 1250469Notes

Reaction equation

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

Participants

Reactant 2

HCID 691404-Chloroquinoline

HCID 147958665-Chloroisoindoline

Product 1

HCID 18326772HCID 18326772, compoundYield 24.2%

Conditions

Temperature: 145 °C

Procedure

A mixture of 4-chloroquinoline (0.245 g, 1.5 mmol) and 5-Chloro-2,3-dihydro-1H-isoindole (0.23 g, 1.5 mmol) was heated at 140-150° C. for 4 hours under Argon then cooled to room temperature. The crude product was recrystallized with methanol to provide 4-(5-Chloro-1,3-dihydro-isoindol-2-yl)-quinoline hydrochloride (0.115 g, 24%) as white solid, m.p. 270-275° C. and MS: m/e=280 (M+).

Workup

temperaturethen cooled to room temperature
customThe crude product was recrystallized with methanol

Sources & evidence

ORD record: ord-dd345a016e0245c18f93fd210988ca53
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339093B1

Reaction notes

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