Benzene → 2-Nitroxymethylpyridine nitrate

Fuming nitric acid (4.1 ml) was added dropwise to acetic anhydride (13.5 ml) with stirring at 5° to 10° C. After the mixture was stirred for 30 minutes at 5° C., 2-hydroxymethylpyridine nitrate (3.3 g) was added in some portions thereto. The resulting mixture was stirred for 3 hours at 0° to 5° C. A mixture of benzene (15 ml) and n-hexane (30 ml) was added thereto. The mixture formed two layers. The upper layer was separated and discarded while the remaining lower layer was again treated with a mixture of benzene (10 ml) and n-hexane (10 ml). After the separation of the layers, the lower layer was again separated, mixed with benzene (10 ml) and made homogeneous with isopropyl alcohol (10 ml). The resulting mixture was allowed to stand overnight in a refrigerator to give crystals. The crystals were collected by filtration and washed with diethyl ether to give white crystals of 2-nitroxymethylpyridine nitrate (2.4 g), mp. 75° to 77° C.

1. stirringAfter the mixture was stirred for 30 minutes at 5° C.
2. stirringThe resulting mixture was stirred for 3 hours at 0° to 5° C
3. additionwas added
4. customThe mixture formed two layers
5. customThe upper layer was separated
6. additionwas again treated with a mixture of benzene (10 ml) and n-hexane (10 ml)
7. customAfter the separation of the layers
8. customthe lower layer was again separated
9. additionmixed with benzene (10 ml)
10. customto give crystals
11. filtrationThe crystals were collected by filtration
12. washwashed with diethyl ether

ORD record

ord-10a159dfdc554b0e9bf8618e2e3940c8

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04540701