HCID 86584269, compound → HCID 86584268, compound

HRID 1280846Notes

Reaction equation

HRID 1280846 reaction equation
[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([C:11](=O)[CH3:12])[CH:8]=[CH:7][C:6]=1[NH:14][C:15]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[C:16]=1[F:24]>CC(O)=O.[Pd]>[CH3:26][N:2]([CH3:1])[C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:14][C:15]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[C:16]=1[F:24]

Participants

4

Reactant 1

HCID 86584269HCID 86584269, compound

Product 1

HCID 86584268HCID 86584268, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N,N-dimethyl-5-acetyl-2-(2′,3′,5′,6′-tetrafluoroanilino)phenylacetamide (30 g, 0.802 mol) is dissolved in HOAc (150 ml) and hydrogenated (55 psi) with a 10% Pd/C (1.5 g) catalyst for 8 hours. The catalyst is removed by filtration through Celite and the filtrate poured into water (500 ml) and EtOAc (500 ml). The organic layer is washed with water (750 ml), neutralized with saturated Na2CO3 solution (500 ml) and washed with brine (500 ml). Evaporation on a rotovap followed by trituration with hexanes gives N,N-dimethyl-5-ethyl-2-(2′,3′,5′,6′-tetrafluoroanilino)phenylacetamide, m.p. 105-106°.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. additionthe filtrate poured into water (500 ml) and EtOAc (500 ml)
  3. washThe organic layer is washed with water (750 ml)
  4. washwashed with brine (500 ml)
  5. customEvaporation on a rotovap

Sources & evidence

ORD record
ord-ad1e11a0c1884a82a780478ea0efd571
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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