Sodium Hydroxide → HCID 59425917, compound

HRID 907092Notes

Reaction equation

HRID 907092 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[N:5]([CH2:16][CH3:17])[CH:4]=1)#[N:2].N1C2C(=CC=C(C(OC)=O)C=2)C=C1.[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[N:5]([CH2:16][CH3:17])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 639844Methyl indole-6-carboxylateHCID 59426010HCID 59426010, compound

Product 1

HCID 59425917HCID 59425917, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 3-cyano-1-ethyl-1H-indole-6-carboxylate (1.60 g, 7.02 mmol), prepared by the method described in example 1A from methyl 1H-indole-6-carboxylate, in THF (35 mL) was treated with 1N NaOH (7.7 mL, 7.7 mmol) and heated at reflux for 2.5 h. After cooling to room temperature, most of the THF was removed and the solution was diluted with H2O and extracted with ether (2×). The ether extracts were discarded. The aqueous phase was then acidified with 6N HCl to pH 2 and then extracted with EtOAc (3×). The EtOAc layers were combined, washed with saturated NaCl and then dried and concentrated to afford 1.43 g (95%) of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. customwas removed
  4. additionthe solution was diluted with H2O
  5. extractionextracted with ether (2×)
  6. extractionextracted with EtOAc (3×)
  7. washwashed with saturated NaCl
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-15e8373da70847acaa85b1373b6faf9b
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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