Sodium Thiosulfate → Ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate

HRID 1604546Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.C1C(=O)N([Br:25])C(=O)C1.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClC(Cl)(Cl)Cl>[Br:25][CH2:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]([CH3:1])=[CH:11]2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 3,6-dimethylquinoline-2-carboxylate (1.0 g) in tetrachloromethane (10 ml) were added N-bromosuccimide (815 mg) and 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile) at ambient temperature under nitrogen atmosphere, and the mixture was heated at 90° C. for 1 hour. The reaction mixture was poured into 5% sodium thiosulfate solution and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane--ethyl acetate) to give ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate (802 mg) as a solid.

Workup

extractionextracted with dichloromethane
washThe organic layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (n-hexane--ethyl acetate)

Sources & evidence

ORD record: ord-24fb130e0fcf4a0faeb07c493421ea52
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994368

Reaction notes

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