Sodium Hydroxide → HCID 89739830, compound

HRID 1526960Notes

Reaction equation

HRID 1526960 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18]CC)=[O:17])=[CH:8]1.[OH-].[Na+]>O1CCCC1>[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([OH:18])=[O:17])=[CH:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89741045HCID 89741045, compound

Product 1

HCID 89739830HCID 89739830, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 1-(o-tolyl)-1H-indole-3-carboxylate (0.789 g, 2.82 mmol), 4N sodium hydroxide aqueous (20 mL) and tetrahydrofuran (20 mL) was stirred at 60° C. for 18 hours. Most solvent was removed and the rest was acidified with 10% hydrochloric acid aqueous to adjust to pH=5. Pale yellow precipitate formed and was collected by filtration. The solid was washed with petroleum ether, dried in vacuo to give 1-(o-tolyl)-1H-indole-3-carboxylic acid as a pale yellow solid (0.675 g, 95%). LRMS (M+H+) m/z: calcd 251.09. found 251.

Workup

  1. customMost solvent was removed
  2. customPale yellow precipitate formed
  3. filtrationwas collected by filtration
  4. washThe solid was washed with petroleum ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b61c5525f9c44461bc4488c136d10a9c
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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