Sodium Hydroxide → 1-(4-fluorobenzyl)-1H-indole-2-carboxylic acid

HRID 83591Notes

Reaction equation

HRID 83591 reaction equation
[F: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-].[Na+]>C(O)C>[F: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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69873711Ethyl 1-(4-fluorobenzyl)-1H-indole-2-carboxylate

Product 1

HCID 186270691-(4-fluorobenzyl)-1H-indole-2-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 1-(4-fluorobenzyl)-1H-indole-2-carboxylate (409 mg, 1.376 mmol) was suspended in ethanol (5 mL) and 7M NaOH (5 mL) and stirred at 50° C. for 3 h. Ethanol content was reduced in vacuo. The solution was then acidified to pH 2 and the precipitate was collected over a filter, washed with a small amount of ice cold-water, air dried on the filter, and then finally vacuum dried to give 360 mg of the title compound as a fine, white powder.

Workup

  1. customthe precipitate was collected over a filter
  2. washwashed with a small amount of ice cold-water, air
  3. customdried on the filter
  4. customfinally vacuum dried

Sources & evidence

ORD record
ord-2269e1bb4d3245dc900a8a4d72cf72b6
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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