Diphenyl Ether → 2-(6-methylquinolin-2-yl)benzoic Acid

HRID 1956769Notes

Reaction equation

HRID 1956769 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:32]=[C:31](C(O)=O)[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:36])[CH:29]=2)[N:24]=1)([OH:16])=[O:15].[OH-].[Na+]>[Cu]=O.O>[CH3:36][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]([OH:16])=[O:15])[CH:32]=[CH:31]2

Participants

6

Reactant 3

HCID 7583Diphenyl EtherHCID 14798Sodium HydroxideHCID 15376151HCID 15376151, compound

Product 1

HCID 98816992-(6-methylquinolin-2-yl)benzoic AcidYield 46.7%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

To 3 ml of diphenyl ether were added 0.5 g of the 2-(2-carboxyphenyl)-6-methyl-4-quinolinecarboxylic acid obtained in Example 2. After adding 6.5 mg of copper oxide, the mixture was heated at 170° C. for 1 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium hydroxide and washed with ethyl acetate. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. After extracting with ethyl acetate, 0.2 g of 2-(6-methylquinolin-2-yl)benzoic acid were obtained. NMR (270 MHz, CD3OD): δ 7.58-8.32 (m,9H); 2.58 (s,3H).

Workup

  1. washwashed with ethyl acetate
  2. customwas formed
  3. extractionAfter extracting with ethyl acetate

Sources & evidence

ORD record
ord-b23834a9a87f46289332221b72908e34
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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