Sodium Hydroxide → 6-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-5-methyl-2-pyridinecarboxamide

HRID 2356630Notes

Reaction equation

HRID 2356630 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][C:10]=2[CH3:17])[CH:7]=1.[OH-:28].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([NH2:16])=[O:28])[CH:12]=[CH:11][C:10]=2[CH3:17])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 684565816-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-5-methyl-2-pyridinecarbonitrile

Product 1

HCID 684567906-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-5-methyl-2-pyridinecarboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-5-methyl-2-pyridinecarbonitrile (127 mg) in 2M sodium hydroxide solution (0.8 ml) and ethanol (4 ml) was stirred under reflux for 2 hours. Solvent was removed in vacuo and water (5 ml) added. The mixture was extracted with ethyl acetate (3×5 ml) and the combined extracts washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound (107 mg, 81%) as a white solid. LC/MS [MH+]=419/421, RT=3.57 min.

Workup

  1. temperatureunder reflux for 2 hours
  2. customSolvent was removed in vacuo and water (5 ml)
  3. additionadded
  4. extractionThe mixture was extracted with ethyl acetate (3×5 ml)
  5. washthe combined extracts washed with brine (5 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4208fb73b58945f2b6a8ecac17cacbd8
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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