Hydroxyamine hydrochloride → 1H-indole-7-carbaldehyde oxime

HRID 1512722Notes

Reaction equation

HRID 1512722 reaction equation
Cl.[NH2:2][OH:3].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH:13]=O)[CH:6]=[CH:5]1>N1C=CC=CC=1>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH:13]=[N:2][OH:3])[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 734136671H-indole-7-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (0.574 g) was added portionwise to a solution of 1H-indole-7-carbaldehyde (1 g) in pyridine (5 ml) at RT. The resulting solution was heated to reflux and kept at that temperature for 1 hour. The solvent was evaporated. Ethyl acetate (50 mL) was added and the resulting solution was washed with aqueous hydrochloric acid (0.5 M, 40 mL). The organic fraction was separated and dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 1H-indole-7-carbaldehyde oxime (D1) as a colorless oil which, upon standing, solidified to give a waxy solid (1.1 g). MS (ES): C9H8N2O requires 160; found 161.1 (M+H+).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customThe solvent was evaporated
  4. additionEthyl acetate (50 mL) was added
  5. washthe resulting solution was washed with aqueous hydrochloric acid (0.5 M, 40 mL)
  6. customThe organic fraction was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe dried solution was concentrated

Sources & evidence

ORD record
ord-5a548ac4f3c84a0a8fbe60225ab04f3a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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