Sodium Hydroxide → 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide

HRID 1510219Notes

Reaction equation

HRID 1510219 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:15]([CH2:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>CO>[NH:15]([CH2:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866297492-anilino-N-[4-(4-pyridinyl)phenyl]acetamide bis(trifluoroacetate)

Product 1

HCID 159813822-anilino-N-[4-(4-pyridinyl)phenyl]acetamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide bis(trifluoroacetate) (11.0 g) in methanol (160 ml) was added 1N sodium hydroxide aqueous solution (51.7 mL) at ambient temperature. After stirring at ambient temperature for 2 hours, methanol was evaporated in vacuo. Water (20 mL) was added to the resulting mixture and the residual solid was collected by filtration. The crystals were washed with water (30 mL) to afford 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide (5.16 g) as colorless crystals.

Workup

  1. custommethanol was evaporated in vacuo
  2. additionWater (20 mL) was added to the resulting mixture
  3. filtrationthe residual solid was collected by filtration
  4. washThe crystals were washed with water (30 mL)

Sources & evidence

ORD record
ord-211ddacd2c074acb9e8f30b2bd11ab4a
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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