Sodium Hydroxide → 3-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide

HRID 2426132Notes

Reaction equation

HRID 2426132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:25])=[C:12]([O:14]C(=O)C2C=CC(F)=C(Cl)C=2)[CH:13]=1)=[O:6].[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:25])=[C:12]([OH:14])[CH:13]=1)=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672127893-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester

Product 1

HCID 575815783-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester (3.93 g, 9 mmol) was dissolved in a mixture of tetrahydrofuran (25 mL), methanol (50 mL) and aqueous 1N sodium hydroxide (9 mL, 9 mmol). The mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure to remove most of the organic solvent. The resulting suspension was diluted with water (45 mL) and saturated aqueous sodium bicarbonate solution (5 mL). After standing for 30 minutes, the precipitate was collected and washed with water and dried to give crude 3-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide as a white powder. (Yield 2.59 g, 103%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove most of the organic solvent
  3. additionThe resulting suspension was diluted with water (45 mL) and saturated aqueous sodium bicarbonate solution (5 mL)
  4. waitAfter standing for 30 minutes
  5. customthe precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b40f82efc5b744df96beda8738cf846b
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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