4,7-Dichloroquinoline → HCID 11382646, compound

HRID 1190907Notes

Reaction equation

HRID 1190907 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:6]([OH:8])[CH:7]=1.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=2)[N:19]=[CH:18][CH:17]=1>CCO>[Cl:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:9][N:10]4[CH2:14][CH2:13][CH2:12][CH2:11]4)=[C:6]([OH:8])[CH:7]=3)=[CH:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 19799804HCID 19799804, compound

Product 1

HCID 11382646HCID 11382646, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-2-(pyrrolidin-1-ylmethyl)phenol (117 mg, 0.61 mmol) and 4,7-dichloroquinoline (143 mg, 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 yellow solid (92 mg, 29% yield). LC-MS: m/z (ESI) 354.1-356.1 [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-6b367161badb4c6283b90877dbd5b25e
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…