Sodium Hydroxide → (4-(2-Benzoxazolyl)amino-3-chlorophenyl)acetic acid

HRID 1372660Notes

Reaction equation

HRID 1372660 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][C:12]=1[Cl:23].[OH-].[Na+]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[Cl:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44606814Ethyl (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetate

Product 1

HCID 17859224(4-(2-Benzoxazolyl)amino-3-chlorophenyl)acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetate (1.70 g, 5.14 mmol) was dissolved in THF (30 ml). To the resulting solution was added 0.5N NaOH (30 ml, 15.0 mmol) under stirring. The resulting mixture was stirred at room temperature for 20 hours. The mixture was concentrated and the residue was acidified with ice-1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetic acid (1.24 g, 80%) as a pale yellow crystalline powder.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 20 hours
  2. concentrationThe mixture was concentrated
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b02e2c1cb314937b0dcf24a336b03d0
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…