Nitric Acid → HCID 23433475, compound

HRID 2121799Notes

Reaction equation

[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([C:8]1[CH:7]=[C:6]2[C:11]([CH:2]([CH3:1])[CH2:3][CH2:4][NH:5]2)=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

1,2,3,4-Tetrahydro-4-methylquinoline (55 mg, 0.337 mmol) was dissolved in sulfuric acid (0.5 mL) and the temperature was lowered to 0° C. To this solution 90% fuming nitric acid (15 mL, 0.337 mmol) was added slowly and the mixture stirred at 0° C. for 1 h, then warmed to rt. The reaction mixture was poured onto 1 g of ice and extracted with dichloromethane (2×5 mL). The organic phase was washed with sat. NaHCO3 (1×3 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 8:2) which afforded 36 mg 952%) of 7-nitro-1,2,3,4-tetrahydro-4-methylquinoline. Data for 7-nitro-1,2,3,4-tetrahydro-4-methylquinoline: 1H NMR (400 MHz, CDCl3) 7.41 (dd, J=8.3, 2.2, 1H), 7.27 (d, J=2.3, 1H), 7.11 (d, J=8.3, 1H), 4.21 (s, 1H), 3.35 (m, 2H), 2.95 (m, 1H), 1.96 (m, 1H), 1.72 (m, 1H), 1.3 (d, J=7.0, 3H).

Workup

customwas lowered to 0° C
additionwas added slowly
temperaturewarmed to rt
extractionextracted with dichloromethane (2×5 mL)
washThe organic phase was washed with sat. NaHCO3 (1×3 mL)
concentrationconcentrated in vacuo to a reddish residue that

Sources & evidence

ORD record: ord-895a816f4a8a4aaaaaa686b79cef935d
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696459B1

Reaction notes

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