Sodium Hydroxide → HCID 59425917, compound

HRID 252484Notes

Reaction equation

HRID 252484 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) is 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 is removed and the solution is diluted with H2O and extracted with ether (2×). The ether extracts are discarded. The aqueous phase is then acidified with 6N HCl to pH 2 and then extracted with EtOAc (3×). The EtOAc layers are 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. customis removed
  4. additionthe solution is 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-13a425b388bf4642a8b09bb8df3538ec
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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