Lithium Hydroxide → 1-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

HRID 83596Notes

Reaction equation

HRID 83596 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([O:18]CC)=[O:17])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([OH:18])=[O:17])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10519288Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate

Product 1

HCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate (2.00 g, 6.37 mmol) and lithium hydroxide (1.53 g, 63.7 mmol) were dissolved in THF:water (10 mL: 20 mL). The reaction was heated at 60° C. overnight. The reaction was cooled and further diluted with water. The reaction was transferred into a separatory funnel and was washed with diethyl ether. The aqueous layer was acidified using 2N HCl to pH 2 where a white solid formed. The suspension was returned to the separatory funnel and was washed with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to obtain pure product as a white solid. Yield: 1.47 g, (White solid).

Workup

  1. temperatureThe reaction was cooled
  2. customThe reaction was transferred into a separatory funnel
  3. washwas washed with diethyl ether
  4. customformed
  5. washwas washed with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain pure product as a white solid

Sources & evidence

ORD record
ord-e1e08fd48440426d91aa1e8b93a2939a
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

Loading…