Acetic Anhydride → 6-Bromo-1H-indole-3-carbonitrile

HRID 1618636Notes

Reaction equation

HRID 1618636 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[NH2:13]O.Cl.CC(OC(C)=O)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 27948306-Bromoindole-3-carbaldehyde

Product 1

HCID 114700676-Bromo-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-bromo-1H-indole-3-carbaldehyde (1.2 g, 5.36 mmol) in pyridine (10 mL) was added NH2OH.HCl (0.424 g, 6.11 mmol) portionwise and the resulting mixture was stirred at rt for 1.5 h. 25 mL of Ac2O was added and the mixture was heated at reflux overnight. After this time the reaction mixture was cooled to rt and poured into ice. The resulting solid was filtered and the product was purified by flash column chromatography to give 6-bromo-1H-indole-3-carbonitrile slightly impure but was used for the next step. Mass Spectrum (ESI) m/e=222 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter this time the reaction mixture was cooled to rt
  4. additionpoured into ice
  5. filtrationThe resulting solid was filtered
  6. customthe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-1249dd06b51c4028ab2e8e0879b64549
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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