Acetic Acid → 1,2-diamino-1,2-dideoxy-D-glucitol

Temperature

4 °C

A solution of 20 g of glucosamine hydrochloride, 20 ml of glacial acetic acid, 80 ml of water and 9.1 ml of phenylhydrazine was heated on a steam bath for one hour, then cooled and filtered. The filtrate was hydrogenated in a Parr apparatus with Raney nickel catalyst until the uptake of hydrogen ceased. This mixture was then filtered, the filtrate was treated with activated charcoal and refiltered through diatomaceous earth, giving a green solution. A 6.31 ml portion of this green solution was treated with 0.24 g of sodium bicarbonate and a suspension of 1.66 g of potassium tetrachloroplatinate in 8 ml of water. The resulting reddish brown solution was stirred overnight, then cooled to 4° C. for 3 hours and the resulting solid collected. A 100 mg portion of this solid was stirred with 15 ml of hot water and then filtered through diatomaceous earth. The filtrate was cooled giving a solid which was collected, giving 90 mg of 1,2-diamino-1,2-dideoxy-D-glucitol, compound with platinum chloride (1:1) as yellow grains, mp 265° C. (dec.).

1. temperaturecooled
2. filtrationfiltered
3. filtrationThis mixture was then filtered
4. additionthe filtrate was treated with activated charcoal
5. customgiving a green solution
6. customthe resulting solid collected
7. stirringA 100 mg portion of this solid was stirred with 15 ml of hot water
8. filtrationfiltered through diatomaceous earth
9. temperatureThe filtrate was cooled
10. customgiving a solid which
11. customwas collected

ORD record

ord-0dd8cedb2cb44f4cb56ff4b974d81c4e

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04587331