4,7-Dichloroquinoline → HCID 11406039, compound

HRID 1190909Notes

Reaction equation

HRID 1190909 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:6]([OH:8])[CH:7]=1.Cl[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>CCO>[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]([CH2:9][N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)=[C:6]([OH:8])[CH:7]=3)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 19799808HCID 19799808, compound

Product 1

HCID 11406039HCID 11406039, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-2-(morpholin-4-ylmethyl)phenol (58 mg, 0.28 mmol) and 4,7-dichloroquinoline (61 mg, 1.1 eq) were refluxed overnight in 1 mL of EtOH. The reaction mixture was then evaporated and purified by flash chromatography (DCM/MeOH/NH4OH 9:1:0.1) to yield expected compound as a brown solid (41 mg, 40% yield). LC-MS: m/z (ESI) 470.1-472.1 [M+H]+

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH 9:1:0.1)

Sources & evidence

ORD record
ord-6d4d4008bf00409f9195767e0fce5190
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…