HCID 19421848, compound → HCID 19421846, compound

HRID 2226525Notes

Reaction equation

HRID 2226525 reaction equation
[C:1]([N:9]([C:16]1[CH:17]=[C:18]([CH2:22][C:23]([O:25]C)=[O:24])[CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[Na+].CO>[C:1]([N:9]([C:16]1[CH:17]=[C:18]([CH2:22][C:23]([OH:25])=[O:24])[CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19421848HCID 19421848, compound

Product 1

HCID 19421846HCID 19421846, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The ester (600 mgs, 1.9 mmol) in 4N sodium hydroxide (20 ml) and methanol (20 ml) was stirred at room temperature overnight. The solvent was evaporated and the residue dissolved in water (10 ml) and acidified with 5N hydrochloric acid. The acidic solution was extracted with dichloromethane (3×50 ml), and the combined organics dried and evaporated to afford 3-(N-benzoylanilino)phenylacetic acid as an oil (550 mgs); δH (CDCl3) 3.59 (2H, s, CH2CO2H), 6.83-7.29 (10H, m, ArH), 7.42-7.48 (3H, m, ArH), 8.09 (2H, d, J 7.2 Hz, ArH).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water (10 ml)
  3. extractionThe acidic solution was extracted with dichloromethane (3×50 ml)
  4. customthe combined organics dried
  5. customevaporated

Sources & evidence

ORD record
ord-e80bb810aa254ee5a1a0fa551ba611fe
Source dataset
uspto-grants-1994_09
Patent number
US05348962

Reaction notes

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