Water → HCID 22370562, compound

HRID 1956771Notes

Reaction equation

HRID 1956771 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18](C(O)=O)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:23])[CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].O.C(=O)([O-])[O-].[Na+].[Na+]>N1C2C(=CC=CC=2)C=CC=1>[CH3:23][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)[CH:19]=[CH:18]2

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 22370556HCID 22370556, compound

Product 1

HCID 22370562HCID 22370562, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Conditions

Temperature
170 °C

Procedure

In 5 ml of quinoline was dissolved 0.1 g of the 2-(4-carboxyphenyl)-6-methyl-4-quinolinecarboxylic acid obtained in Example 16 and solution was heated at 170° C. for 0.5 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium carbonate and washed with toluene. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. After extracting with dichloromethane, 0.06 g of 4-(6-methylquinolin-2-yl)benzoic acid were obtained. NMR (270 MHz, CD3OD): δ 7.5-8.3 (m,9H); 2.56 (s,3H).

Workup

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

Sources & evidence

ORD record
ord-e861e15970084e7d881e26f28be8bd46
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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