Sodium Hydroxide → 1H-indole-2-carbonitrile

HRID 1601060Notes

Reaction equation

HRID 1601060 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:12])=O.[OH-].[Na+]>ClP(=O)(Cl)C1C=CC=CC=1>[C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)#[N:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5948321H-Indole-2-carboxamide

Product 1

HCID 37875991H-indole-2-carbonitrileYield 90.2%

Reagents, catalysts & solvents 1

HCID 69990Phenylphosphonic dichlorideSolvent

Procedure

A solution of indole-2-carboxamide (3.02 g, 18.8 mmol) in dichlorophenylphosphine oxide (20 mL) was heated at 80° C. overnight. The cooled reaction mixture was then poured over 100 mL ice and the pH was adjusted to 11 with 50% aqueous sodium hydroxide. Extraction with ethyl acetate followed by concentration in vacuo gave an off-white solid which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield the title compound (2.41 g, 90%): 1H NMR (400 MHz, DMSO-d6) δ 7.68 (d, 1H), 7.46 (d, 1H), 7.36 (s, 1H), 7.34 (t, 1H), 7.14 (t, 1H).

Workup

  1. customThe cooled reaction mixture
  2. extractionExtraction with ethyl acetate
  3. concentrationfollowed by concentration in vacuo
  4. customgave an off-white solid which
  5. customwas purified by silica gel chromatography (1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f8170f6a20dc42f399bf99443b5f9507
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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