Water → Methyl 4-bromoquinoline-6-carboxylate

HRID 1699896Notes

Reaction equation

CO[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.P(Br)(Br)[Br:18].O.[OH-].[Na+]>CN(C=O)C>[Br:18][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-methoxy-6-quinolinecarboxylate (910 mg) in DMF (7 ml) was added phosphorus tribromide (1.57 ml) while stirring under ice-cooling. DMF (7 ml) was added and the mixture was heated at 80° C. for 3 hr. To the reaction mixture was added water (50 ml) and the reaction mixture was made weak basic with a 1N aqueous sodium hydroxide solution. The resulting precipitate was collected by filtration and purified by silica gel column chromatography (eluent: chloroform-methanol=100/0-100/1) to give the object compound (420 mg) as a yellow powder.

Workup

temperaturecooling
filtrationThe resulting precipitate was collected by filtration
custompurified by silica gel column chromatography (eluent: chloroform-methanol=100/0-100/1)

Sources & evidence

ORD record: ord-6fa9b61c34984705979211bc133ba049
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348474B1

Reaction notes

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