Benzoic acid, 4-(acetyloxy)- → HCID 22132696, compound

HRID 1857155Notes

Reaction equation

HRID 1857155 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.[C:23]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1)(=[O:25])[CH3:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[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:31]([C:30]2[CH:29]=[CH:28][C:27]([O:26][C:23](=[O:25])[CH3:24])=[CH:35][CH:34]=2)=[O:32])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132696HCID 22132696, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (110 mg) and commercially available 4-acetoxybenzoic acid (207 mg) were dissolved in N,N-dimethylformamide (6 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (223 mg) was added, and the admixture was stirred at room temperature for 7 hours. The reaction mixture was then purified in the same manner as described in Example 51 to obtain 123 mg of the title compound (yield: 72%).

Workup

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

Sources & evidence

ORD record
ord-692fc6d43e2b4d038253167f3657f0b4
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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