Triethylamine → Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 1940170Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

2-Amino-3',4,4',5-tetramethoxybenzophenone hydrochloride (36.0 g) and ethyl 4-chloroacetoacetate (21.4 g) were stirred in ethanol (350 ml) under reflux for 7 hours. After completion of the reaction, triethylamine (10.6 g) was added dropwise at a temperature not over 20° C. and the mixture was stirred at 5° C. for 1 hour. The crystals were collected by filtration, washed twice with 50 ml each of ethanol and dried under reduced pressure to provide ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (41.0 g; yield 92%).

Workup

temperatureunder reflux for 7 hours
additionwas added dropwise at a temperature not over 20° C.
filtrationThe crystals were collected by filtration
washwashed twice with 50 ml each of ethanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-7bb3de3100d24c76a5cd889b688142ba
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698699

Reaction notes

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