Water → 2-(6-methylquinolin-2-yl)benzoic Acid

HRID 1956767Notes

Reaction equation

HRID 1956767 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:19]=[C:18](C(O)=O)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:23])[CH:16]=2)[N:11]=1)([OH:3])=[O:2].O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[CH3:23][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:1]([OH:3])=[O:2])[CH:19]=[CH:18]2

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 15376151HCID 15376151, compound

Product 1

HCID 98816992-(6-methylquinolin-2-yl)benzoic AcidYield 35%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

In 1 ml of N,N-dimethylacetamide was dissolved 0.2 g of the 2-(2-carboxyphenyl)-6-methyl-4-quinolinecarboxylic acid obtained in Example 2 and heated at 180° C. for 1 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium carbonate and washed with dichloromethane. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. After extracting with dichloromethane, 60 mg of 2-(6-methylquinolin-2-yl)benzoic acid was obtained. NMR (270 MHz, CD3OD): δ 7.58-8.32 (m,9H); 2.58 (s,3H).

Workup

  1. washwashed with dichloromethane
  2. customwas formed
  3. extractionAfter extracting with dichloromethane

Sources & evidence

ORD record
ord-02b39d5d97064e7899298178b263ce9b
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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