Sodium Hydroxide → HCID 13105472, compound

HRID 1777517Notes

Reaction equation

HRID 1777517 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13105471HCID 13105471, compound

Product 1

HCID 13105472HCID 13105472, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-(3-(trifluoromethyl)phenylamino)benzoate (0.334 g; 1.08 mmol) in dioxane (14 mL) was added a solution of sodium hydroxide (0.130 g; 3.24 mmol) in water (3.24 ml). The mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure to remove the dioxane. The aqueous solution was acidified with 6N hydrochloric acid, extracted with ethyl acetate (2×100 mL), dried and concentrated under reduced pressure to provide 0.303 g (99%) of 3-(3-(trifluoromethyl)phenylamino)benzoic acid which was directly used in the next step.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the dioxane
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3faf4ed0137141e9b119130a59db6a03
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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