Sodium Hydroxide → HCID 89739830, compound

HRID 2206476Notes

Reaction equation

HRID 2206476 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-4effe6a41e7d42fd9abefac8ec665a1d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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