Nitric Acid → HCID 59003390, compound

Temperature

0 °C

A solution of 2,2,6-trimethyl-1,2,3,4-tetrahydroquinoline (0.66 g, 3.8 mmol) in 10 mL of concentrated sulfuric acid was cooled to 0° C. in an ice bath. To this solution was added dropwise 1.0 mL 90% fuming nitric acid. The resulting mixture was stirred at 0° C. for 30 min., poured onto 150 mL of ice-water, neutralized to pH=7 with K2CO3 and extracted with CH2Cl2 (3×200 mL). The combined organic layers were washed with water (2×300 mL), saturated aqueous NaHCO3 (300 mL) and brine (300 mL). The solution was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (Silica gel, 15 to 20% ethyl acetate/hexane gradient elution) to give 2,2,6-trimethyl-7-nitro-1,2,3,4-tetrahydro-quinoline. 1H NMR (500 MHz, CDCl3): 8.03 (s, 1H), 7.05 (s, 1H), 2.85 (td, J=6.6, 1.1 Hz, 2H), 2.17 (s, 3H), 1.76 (t, J=6.6 Hz, 2H), 1.35 (s, 6H).

1. additionTo this solution was added dropwise 1.0 mL 90%
2. extractionextracted with CH2Cl2 (3×200 mL)
3. washThe combined organic layers were washed with water (2×300 mL), saturated aqueous NaHCO3 (300 mL) and brine (300 mL)
4. dry with materialThe solution was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash column chromatography (Silica gel, 15 to 20% ethyl acetate/hexane gradient elution)

ORD record

ord-0d2a970cd6774a99a1b2d51e6aa31c1c

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865918B2