Nitric Acid → 3-Acetylamino-adamantane-1-carboxylic acid

Temperature

0 °C

To a 10-L reactor was added 1-adamantanecarboxylic acid (503 g, 2.79 mol; TCI America, Wellesley Hills, Mass., USA) and 70% nitric acid (400 mL, 6.72 mol), and the resulting suspension was cooled at 0° C. with a recirculating chiller. To the mixture was slowly added 98% sulfuric acid (3.00 L, 55.5 mol) at such a rate that the temperature was kept below 10° C. Once the addition completed, acetonitrile (2.00 L, 38.5 mol) was added at such a rate that the temperature was kept below 10° C. After all the acetonitrile was added, the reaction was stirred at 0° C. for 1 hour. The crude reaction was then added to a 20-L reactor filled with about 10-L of ice mixed with a small amount of water and the resulting mixture was stirred and allowed to warm to room temperature. The solids were then filtered and washed with water. More solids precipitated from the acidic aqueous layer and these were filtered as well and washed with water. The combined solid material was then dried under high vacuum at 50° C. for 2 days to afford 432 g (73%) of the title compound, 3-acetylamino-adamantane-1-carboxylic acid, as a white solid.

1. customwas kept below 10° C
2. additionOnce the addition
3. customwas kept below 10° C
4. customThe crude reaction
5. additionwas then added to a 20-L reactor
6. stirringthe resulting mixture was stirred
7. temperatureto warm to room temperature
8. filtrationThe solids were then filtered
9. washwashed with water
10. customMore solids precipitated from the acidic aqueous layer
11. filtrationthese were filtered as well and
12. washwashed with water
13. customThe combined solid material was then dried under high vacuum at 50° C. for 2 days

ORD record

ord-5485713c12764b90b6801a4e9d0f774c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389519B2