Reaction #5099

Reaction equation

6-chloroacetylaminomethyl-2,3-dihydro-7-hydroxy-4-methyl-1H-indene-1-one

hydroxylamine hydrochloride

pyridine

ethanol

water

→

(2,3-dihydro-7-hydroxy-1-hydroxyimino-4-methyl-1H-indene-6yl)-methylaminocarbonylmethylpyridinium chloride

Conditions

Workup

1. 1
   Otherthe solvent was removed by evaporation under a reduced pressure
2. 2
   Otherto the residue thus obtained
3. 3
   Temperaturecooled
4. 4
   Othercrystallized
5. 5
   FiltrationThe crystals were collected by filtration
6. 6
   Washwashed with water
7. 7
   Otherrecrystallized from water

Procedure

200 Grams of 6-chloroacetylaminomethyl-2,3-dihydro-7-hydroxy-4-methyl-1H-indene-1-one, 77.9 g of hydroxylamine hydrochloride, 300 ml of pyridine and 1,800 ml of ethanol were refluxed for 3 hours. After the reaction was completed, the solvent was removed by evaporation under a reduced pressure, then to the residue thus obtained was added 2 liters of water and the mixture was stirred vigorously, cooled and crystallized. The crystals were collected by filtration, washed with water, and recrystallized from water to obtain 167 g of (2,3-dihydro-7-hydroxy-1-hydroxyimino-4-methyl-1H-indene-6yl)-methylaminocarbonylmethylpyridinium chloride. Colorless flake-like crystals. Melting point: 279° C. (Decomposed).

Source