Water → HCID 67429372, compound

HRID 1661814Notes

Reaction equation

HRID 1661814 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2.O.C(=O)([O-])[O-:18].[K+].[K+]>COCCOC>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([OH:18])[CH2:10][CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514202Methyl 6-quinolineacetate

Product 1

HCID 67429372HCID 67429372, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

m-Perchlorobenzoic acid (6.85 g, 39.8 mmol) was added to a solution of commercially available quinolin-6-yl-acetic acid methyl ester (5.00 g, 24.8 mmol) in 1,2-dimethoxyethane at room temperature and stirred for 2 hours. Water was added and the solution was basified to pH 9-10 with saturated potassium carbonate and the product was extracted with ethyl acetate to give quantitative yield of (1-hydroxy-quinolin -6-yl)-acetic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, 1H, J=8.4 Hz), 7.93 (d, 1H, J=8.4 Hz), 7.65 (m, 1H), 7.60 (m, 1H), 7.32 (d, 1H, J=8.8 Hz), 7.19 (s, 1H), 3.74 (s, 2H), 3.65 (s, 3H).

Workup

  1. extractionthe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-e5973494e52f47608222b835f928f2d5
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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