Water → 4-[(2-Methylquinolin-4-yl)methoxy]benzoic acid

HRID 517521Notes

Reaction equation

HRID 517521 reaction equation
[OH-].[Na+].O.[CH3:4][C:5]1[CH:14]=[C:13]([CH2:15][O:16][C:17]2[CH:32]=[CH:31][C:20]([C:21]([O:23]CC3C=CC=CC=3)=[O:22])=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1>O1CCCC1.CO>[CH3:4][C:5]1[CH:14]=[C:13]([CH2:15][O:16][C:17]2[CH:32]=[CH:31][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 67056944HCID 67056944, compound

Product 1

HCID 220327754-[(2-Methylquinolin-4-yl)methoxy]benzoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.3 ml (18.6 mmol) of an 8N aqueous solution of sodium hydroxide and 5 ml of water are added to a solution of 3.6 g (9.3 mmol) of benzyl 4-(2-methylquinolin-4-ylmethoxy)benzoate diluted in 20 ml of tetrahydrofuran and 30 ml of methanol. The reaction medium is stirred at ambient temperature for 48 h then 1 ml of an 8N aqueous solution of sodium hydroxide is added and the mixture is heated at 70° C. for 5 h. After evaporation of the tetrahydrofuran, water and a 1N aqueous solution of acetic acid are added. The suspension is stirred overnight at ambient temperature then filtered. The solid obtained is dried under vacuum at 40° C. for 6 h. 2.2 g (81%) of 4-(2-methylquinolin-4-ylmethoxy)benzoic acid are obtained in the form of a white solid.

Workup

  1. temperaturethe mixture is heated at 70° C. for 5 h
  2. customAfter evaporation of the tetrahydrofuran, water
  3. additiona 1N aqueous solution of acetic acid are added
  4. stirringThe suspension is stirred overnight at ambient temperature
  5. filtrationthen filtered
  6. customThe solid obtained
  7. customis dried under vacuum at 40° C. for 6 h

Sources & evidence

ORD record
ord-f7c789ba8bf442a9ae870cd428d7e24d
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

Loading…