Sodium Hydroxide → HCID 18451528, compound

HRID 1270801Notes

Reaction equation

HRID 1270801 reaction equation
CN(C)[C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:17][C:16]=1[F:28].[OH-:31].[Na+]>CCO>[CH:11]1([C:9]2[CH:8]=[CH:7][C:6]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[CH:17][C:16]=3[F:28])=[C:5]([CH2:4][C:3]([OH:29])=[O:31])[CH:10]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593361HCID 86593361, compound

Product 1

HCID 18451528HCID 18451528, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,N-dimethyl-5-cyclopropyl-2-[2′-fluoro-4′-(4-fluorophenyl)anilino]phenylacetamide (575 mg) in 10 mL of 4 N NaOH and 20 mL of EtOH is heated overnight at 80° C. After cooling, the EtOH is removed under reduced pressure and the residue is diluted with EtOAc and cold water. The mixture is cooled in an ice bath and cold 2.5 N HCl is added until the pH of the aqueous layer reaches 2. The organic phase is separated, washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid is purified by flash chromatography eluting with 10%, then 20%, then 30% EtOAc in hexane to give the title product, m.p. 182–183° C.

Workup

  1. temperatureAfter cooling
  2. customthe EtOH is removed under reduced pressure
  3. additionthe residue is diluted with EtOAc and cold water
  4. temperatureThe mixture is cooled in an ice bath
  5. additioncold 2.5 N HCl is added until the pH of the aqueous layer
  6. customThe organic phase is separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customto give a brown solid
  11. customThe solid is purified by flash chromatography
  12. washeluting with 10%

Sources & evidence

ORD record
ord-3c59d826046e4f35ae39a36ffb279948
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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