Hydroxyamine hydrochloride → 3-Formylindole-4-carboxylic acid methyl ester oxime

HRID 1605262Notes

Reaction equation

HRID 1605262 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7]([CH:14]=[O:15])=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=O.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3](=[N:17][OH:18])[C:5]1[C:6]2[C:7]([CH:14]=[O:15])=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 12396096methyl 3-formyl-1H-indole-4-carboxylate

Product 1

HCID 867332223-Formylindole-4-carboxylic acid methyl ester oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-formyl -4-indolecarboxylic acid methyl ester (2.03 g), described in Example 1, 10 ml of a 5M aqueous solution of hydroxylamine hydrochloride, 10 of 5M aqueous sodium acetate and 20 ml. of methanol is stirred at 45°-55°C for 1 hr. The precipitate is collected and washed with cold water. Recrystallization from methanol-water gives the title compound, mp 178°-179°C.

Workup

  1. customThe precipitate is collected
  2. washwashed with cold water
  3. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-dc278f365f404a08bfdb845ea412e462
Source dataset
uspto-grants-1976_04
Patent number
US03950343

Reaction notes

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