Hydrochloric Acid → Benzyl 6-(benzyloxy)quinoline-2-carboxylate

HRID 1497556Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=1)=[O:13])[CH:6]=[CH:5]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-hydroxyquinoline-2-carboxylic acid (2.00 g) in N,N-dimethylformamide (20.0 mL) were added potassium carbonate (3.07 g) and benzyl bromide (3.02 mL), followed by stirring at 50° C. for 6 hours. The reaction mixture was left to be cooled, 1 M hydrochloric acid, ethyl acetate, and tetrahydrofuran were added thereto, and the organic layer was extracted. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by hexane-ethyl acetate to obtain benzyl 6-(benzyloxy)quinoline-2-carboxylate (1.80 g).

Workup

waitThe reaction mixture was left
temperatureto be cooled
extractionthe organic layer was extracted
washThe organic layer was washed with water
dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by hexane-ethyl acetate

Sources & evidence

ORD record: ord-b36b13778c40405584312bdbdbe848c2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199927B2

Reaction notes

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