Reaction #52596

Reaction equation

Chloral hydrate

hydroxylamine hydrochloride

4-anisidine

hydrochloric acid

→

N-(2-hydroximino-acetyl)anisidine

Yield 85.2%

Solvents

water

sodium sulfate

water

water

Conditions

Workup

1. 1
   Otherwas held at 60° C
2. 2
   workup.ADDITIONThe first solution was added to the second and the mixture
3. 3
   Temperaturerefluxed for 2 minutes after which it
4. 4
   Temperaturewas cooled slowly to room temperature
5. 5
   Temperaturecooled in an ice bath
6. 6
   FiltrationThe tan precipitate was collected by vacuum filtration
7. 7
   Washwashed with water
8. 8
   Otherdried under vacuum

Procedure

Chloral hydrate (9.6 g) was dissolved in 200 mL of water containing 83 g of sodium sulfate. The solution was warmed to 60° C., a solution of 11.4 g of hydroxylamine hydrochloride in 50 mL of water was added and the mixture was held at 60° C. In a separate flask, 6.4 g of 4-anisidine and 4.3 mL of concentrated hydrochloric acid in 80 mL of water was warmed to 80° C. The first solution was added to the second and the mixture refluxed for 2 minutes after which it was cooled slowly to room temperature and then cooled in an ice bath. The tan precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 8.6 g (85% yield) of N-(2-hydroximino-acetyl)anisidine.

Source