Ethanol → 2-Benzyl-7-bromo-3-methoxyquinoline

HRID 1359418Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][O:12][CH2:13][C:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.[OH-].[K+].C(O)C>O>[CH2:16]([C:14]1[C:13]([O:12][CH3:11])=[CH:4][C:3]2[C:2](=[CH:9][C:8]([Br:10])=[CH:7][CH:6]=2)[N:1]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3.3 g of 2-amino−4-bromobenzaldehyde, 3.3 g of 1-methoxy-3-phenylacetone, an aqueous potassium hydroxide solution (10 g of potassium hydroxide was dissolved in 10 ml of water) and 20 ml of ethanol was heated under stirring at 100° C. for 4 hours in a sealed tube. After cooling as it was, the reaction solution was poured into water and the mixture was extracted with diethyl ether. The organic phase was washed with brine and the solvent was removed. The residue was crystallized from hexane/ethyl acetate, to give 3.7 g of the target compound.

Workup

temperatureAfter cooling as it
extractionthe mixture was extracted with diethyl ether
washThe organic phase was washed with brine
customthe solvent was removed
customThe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-389764ae11ae42609d162513a4b53a03
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599917B1

Reaction notes

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