Hydroxyamine hydrochloride → 6-Methyl-1H-indole-3-carbaldehyde oxime

HRID 1432499Notes

Reaction equation

HRID 1432499 reaction equation
[CH3:1][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.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[N:14][OH:15])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 47779026-Methylindole-3-carboxaldehyde

Product 1

HCID 1363955696-Methyl-1H-indole-3-carbaldehyde oximeYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-methyl-1H-indole-3-carbaldehyde (0.96 g, Lit. 20) in ethanol (30 ml) was added at 22° C. hydroxylamine hydrochloride (0.46 g) and sodium acetate (0.54 g) and the mixture was stirred for 3 h. The mixture was evaporated and the residue triturated with water and dichloromethane/n-heptane (1:1) and dried to give the title compound (0.96 g) as a pink solid. MS: 175.3 ([M+H]+).

Workup

  1. customThe mixture was evaporated
  2. customthe residue triturated with water and dichloromethane/n-heptane (1:1)
  3. customdried

Sources & evidence

ORD record
ord-2801173243c84c94982b6927a1aebbb3
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

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