HCID 19421848, compound → HCID 19421846, compound

HRID 744127Notes

Reaction equation

HRID 744127 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-63b6282e86ce4da88b0ea6dd2804ba5a
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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