Sodium Hydroxide → 2-(2',3',5',6'-Tetrafluoro-4'-phenylanilino)phenylacetic Acid

HRID 1270800Notes

Reaction equation

HRID 1270800 reaction equation
CN(C)[C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:14]([F:26])[C:13]=1[F:27].[OH-:30].[Na+]>CCO.O>[F:18][C:17]1[C:16]([F:19])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([F:26])=[C:13]([F:27])[C:12]=1[NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][C:3]([OH:30])=[O:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86593360N,N-Dimethyl-2-(2',3',5',6'-tetrafluoro-4'-phenylanilino)phenylacetamide

Product 1

HCID 102488732-(2',3',5',6'-Tetrafluoro-4'-phenylanilino)phenylacetic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of N,N-dimethyl-2-(2′,3′,5′,6′-tetrafluoro-4′-phenylanilino)phenylacetamide (2.7 g, 6.7 mmol) and NaOH (3.0 g, 72 mmol) in EtOH (100 mL) and water (20 mL) is heated at reflux temperature for 14 hours. After cooling to room temperature, most of the ethanol is removed by rotary evaporator. Ice water (250 mL) and ice cold Et2O (250 mL) are added and the organic phase is separated and washed with ice cold 1 N HCl (200 mL) and then brine (100 mL). The organic solution is dried (MgSO4) and evaporated by rotary evaporator taking care not to warm above 50° C. The title compound is obtained by trituration of the residue with hexane (m.p. 180–181° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 14 hours
  3. customis removed by rotary evaporator
  4. additionIce water (250 mL) and ice cold Et2O (250 mL) are added
  5. customthe organic phase is separated
  6. washwashed with ice cold 1 N HCl (200 mL)
  7. dry with materialThe organic solution is dried (MgSO4)
  8. customevaporated by rotary evaporator
  9. temperatureto warm above 50° C

Sources & evidence

ORD record
ord-51a2d4c9af3d44f2b735cb429dfc4a8f
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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