Sodium Hydroxide → 2-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid

HRID 1446876Notes

Reaction equation

HRID 1446876 reaction equation
[CH3:1][N:2]([C:13]1[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.[OH-].[Na+]>C(O)(C)C.O>[CH3:1][N:2]([C:13]1[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13314823Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

Product 1

HCID 133148242-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acidYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate (10.0 g; see Example 7) was suspended in isopropyl alcohol (50 ml) and a solution of sodium hydroxide (1.12 g) in water (50 ml) was added over a period of 45 minutes. Further isopropyl alcohol (60 ml) was added and the mixture was stirred at room temperature for a period of 48 hours. The alcohol was removed by distillation under reduced pressure, the residue was dissolved in water and the aqueous solution was acidified to pH 4 by the addition of aqueous 2 M hydrochloric acid. The precipitate was collected by filtration, dried and recrystallised from ethyl acetate to give the title compound (5.83 g; 63%), mp 152°-154° C. The pmr spectrum of the compound was consistent with the assigned structure.

Workup

  1. customThe alcohol was removed by distillation under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additionthe aqueous solution was acidified to pH 4 by the addition of aqueous 2 M hydrochloric acid
  4. filtrationThe precipitate was collected by filtration
  5. customdried
  6. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-10b0c5d639b749809c0ac19467ed0a9f
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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