1H-indole-6-carbonitrile → HCID 178513228, compound

HRID 1512803Notes

Reaction equation

HRID 1512803 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[CH:11]=[CH:10]1>CCO>[OH:3][NH:2][C:18]([C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][NH:9]2)=[CH:13][CH:14]=1)=[NH:19]

Participants

5

Reactant 3

HCID 851461H-indole-6-carbonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178513228HCID 178513228, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (4.7 g) and sodium bicarbonate (8.6 g) were added to a solution of 1H-indole-6-carbonitrile (4.8 g) in EtOH (70 mL) successively. The reaction mixture was heated to reflux and stirred for 36 hours. The inorganic percipitate was filtered off. The solid was washed with EtOH (30 mL). The filtrate was concentrated to afford N-hydroxy-1H-indole-6-carboximidamide (D100) (6.3 g) as a yellow solid. No purification was attempted. MS (ES): C9H9N3O requires 175; found 176.2 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationThe inorganic percipitate was filtered off
  4. washThe solid was washed with EtOH (30 mL)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f2946ac3f37d404eb908caa5039eeb92
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…