Sodium Hydroxide → 2-(2-Bromophenylamino)-6-benzoxazolylacetic acid

HRID 1372614Notes

Reaction equation

HRID 1372614 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([O:21]CC)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58779103Ethyl 2-(2-bromophenylamino)-6-benzoxazolylacetate

Product 1

HCID 587783952-(2-Bromophenylamino)-6-benzoxazolylacetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 2-(2-bromophenylamino)-6-benzoxazolylacetate (3.82 g, 10.6 mmol) was dissolved in THF-methanol (1:1, 40 ml). To the resulting solution, 1.0M-NaOH (52.0 ml, 52.0 mmol) was added, followed by stirring at room temperature for 1.5 hours. To the residue, which had been obtained by distilling off the solvent under reduced pressure, was acidified with 1.0N-HCl. The crystals thus obtained were collected by filtration under reduced pressure, washed with water and dried overnight under reduced pressure at 60° C., whereby 2-(2-bromophenylamino)-6-benzoxazolylacetic acid (3.40 g, 93%) was obtained as a white crystalline powder.

Workup

  1. customTo the residue, which had been obtained
  2. distillationby distilling off the solvent under reduced pressure
  3. customThe crystals thus obtained
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried overnight under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-35dab7dd264f4efa9603ad0f7f6aef0c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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