4-Butoxybenzoyl chloride → 4-Butoxy-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamide

HRID 1857148Notes

Reaction equation

HRID 1857148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[CH2:23]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH3:26]>C(N(CC)CC)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:32]([C:31]2[CH:35]=[CH:36][C:28]([O:27][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:29][CH:30]=2)=[O:33])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 1185614-Butoxybenzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 221326314-Butoxy-N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}benzamideYield 41%

Reagents, catalysts & solvents 1

HCID 21882572Triethylamine methylene chlorideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was suspended in triethylamine/methylene chloride (3 ml/2 ml), commercially available 4-butoxybenzoyl chloride (0.07 ml) was added, and the admixture was stirred at room temperature for 30 hours. The reaction mixture was then purified in the same manner as described in Example 62 to obtain 34 mg of the title compound (yield: 41%).

Workup

  1. customThe reaction mixture was then purified in the same manner

Sources & evidence

ORD record
ord-01b844a4e0b64c96a4e6371d5558b2e2
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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