Ethanol → HCID 59314286, compound

HRID 1047865Notes

Reaction equation

HRID 1047865 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([F:26])[F:25])=[CH:19][C:18]=2[CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].CCO>O>[F:25][CH:24]([F:26])[O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:28])=[C:18]([CH3:27])[CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 59314384HCID 59314384, compound

Product 1

HCID 59314286HCID 59314286, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 2-(4-difluoromethoxy-2-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (243) (301 mg, 0.77 mmol), KOH (50% aqueous solution, 1.73 g, 15.5 mmol), EtOH (10 mL) and water (1 mL) are stirred in a 20 mL vial at 50° C. for 30 min. After concentration in vacuo, the residue is dissolved in water (10 mL) and acidified with conc. HCl until no more white precipitate came out of the water. The filtration affords 2-(4-difluoromethoxy-2-methyl-benzoylamino)-indan-2-carboxylic acid (244) as white solid (245 mg, 88%).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue is dissolved in water (10 mL)
  3. filtrationThe filtration

Sources & evidence

ORD record
ord-b1723302e60f4e7eb127bf982e285347
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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