Methanol → 2-(hydroxymethyl)-1H-indole-5-carbonitrile

HRID 1512739Notes

Reaction equation

HRID 1512739 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18](OCC)=[O:19])=[CH:12]2)#[N:8].CO>C1COCC1>[OH:19][CH2:18][C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:7]#[N:8])=[CH:17][CH:16]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 4714953Ethyl 5-cyanoindole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 135679562-(hydroxymethyl)-1H-indole-5-carbonitrileYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0 M in THF, 5 mL) was added to a solution of ethyl 5-cyano-1H-indole-2-carboxylate (D21) (1 g) in THF (100 mL). The reaction mixture was stirred for 15 min at RT. MeOH was added to quench the reaction. The solvent was evaporated. EtOAc (500 mL) was added. The organic solution was washed with aqueous HCl (300 mL), then was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 2-(hydroxymethyl)-1H-indole-5-carbonitrile (D24) (600 mg) as a pale orange oil. MS (ES): C10H8N2O requires 172; found 173.2 (M+H+)

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solvent was evaporated
  4. additionEtOAc (500 mL) was added
  5. washThe organic solution was washed with aqueous HCl (300 mL)
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationThe dried solution was concentrated

Sources & evidence

ORD record
ord-8b4022c50aac4f278f6a4019191ae3e8
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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