Sodium Hydroxide → 2-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

HRID 1594890Notes

Reaction equation

HRID 1594890 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:16]C(=O)C)[C:10]2[N:11]([CH3:15])[CH:12]=[N:13][CH:14]=2)=[CH:5][C:4]=1[F:20])#[N:2].[OH-].[Na+]>C1COCC1.O>[F:20][C:4]1[CH:5]=[C:6]([CH:9]([OH:16])[C:10]2[N:11]([CH3:15])[CH:12]=[N:13][CH:14]=2)[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53810060Acetic acid (4-cyano-3-fluoro-phenyl)-(3-methyl-3h-imidazol-4-yl)-methyl ester

Product 1

HCID 185332012-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl ester (as described in Step D above) (1.26 g, 4.59 mmol) and NaOH (5.5 mL, 5.5 mmol) were dissolved in THF (15 mL) and H2O (25 mL). After 1h, the reaction was diluted with satd. NaHCO3 solution, extracted with CH2Cl2 (3×), dried (MgSO4) and concentrated to give the title compound.

Workup

  1. extractionNaHCO3 solution, extracted with CH2Cl2 (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7fd1ec0231634531a74d13b387760492
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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