Water → HCID 22370538, compound

HRID 1956770Notes

Reaction equation

HRID 1956770 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](=[C:13]([CH3:23])[CH:14]=[CH:15][CH:16]=2)[N:11]=1)([OH:3])=[O:2].O.[OH-].[Na+]>N1C2C(=CC=CC=2)C=CC=1>[CH3:23][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=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 14798Sodium HydroxideHCID 22370537HCID 22370537, compound

Product 1

HCID 22370538HCID 22370538, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Conditions

Temperature
170 °C

Procedure

In 5 ml of quinoline was dissolved 0.1 g of the 2-(2-carboxyphenyl)-8-methyl-4-quinolinecarboxylic acid obtained in Example 11 and the solution was heated at 170° C. for 1.5 hours. Then the reaction mixture was poured into water, made alkaline by adding sodium hydroxide and washed with toluene. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. After extracting with dichloromethane, 0.05 g of 2-(8-methylquinolin-2-yl)benzoic acid were obtained. NMR (270 MHz, CD3OD): δ 7.5-8.3 (m,9H); 2.63 (s,3H).

Workup

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

Sources & evidence

ORD record
ord-477eb241144647d3b7539aefc5a631f4
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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