Ethanol → HCID 25161047, compound

HRID 1047855Notes

Reaction equation

HRID 1047855 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[C:18]=2[CH3:25])[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>[C:23]([C:19]1[C:18]([CH3:25])=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:26])#[N:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 59314291HCID 59314291, compound

Product 1

HCID 25161047HCID 25161047, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 2-(3-cyano-2-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (3) (310 mg, 0.89 mmol), KOH (50% aqueous solution, 2 g, 17.8 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 (5 mL) and acidified with conc. HCl until no more white precipitate came out of the water. The filtration affords 2-(3-cyano-2-methyl-benzoylamino)-indan-2-carboxylic acid (238) as white solid (270 mg, 95%).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue is dissolved in water (5 mL)
  3. filtrationThe filtration

Sources & evidence

ORD record
ord-7e9508a68ee94dfe9341de8d24d8de57
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…