4,7-Dichloroquinoline → HCID 67247174, compound

HRID 1190919Notes

Reaction equation

HRID 1190919 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:6]([CH2:8][OH:9])[CH:7]=1.[Cl:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>C(O)CCCC>[ClH:16].[Cl:27][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)=[C:6]([CH2:8][OH:9])[CH:7]=3)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 23136616(5-Amino-2-morpholinophenyl)methanol

Product 1

HCID 67247174HCID 67247174, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

[5-Amino-2-(morpholin-4-yl)phenyl]methanol (1.21 g, 5.80 mmol) and 4,7-dichloroquinoline (1.38 g, 6.98 mmol) were refluxed in 10 mL of n-pentanol for 3 h. The reaction mixture was then cooled to room temperature and the hydrochloride precipitate was removed by filtration to yield expected compound as a yellow powder (1.90 g, 80% yield). LC-MS: m/z (ESI) 370.3 [M+H]+.

Workup

  1. customthe hydrochloride precipitate was removed by filtration

Sources & evidence

ORD record
ord-19869fe633c74b21b39622b7f67bdc32
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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