Nitric Acid → HCID 23433475, compound

HRID 1604812Notes

Reaction equation

HRID 1604812 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

4

Reactant 2

HCID 944Nitric AcidHCID 86854Quinoline, 1,2,3,4-tetrahydro-4-methyl-

Product 1

HCID 23433475HCID 23433475, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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 (52%) 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=8.32, 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

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

Sources & evidence

ORD record
ord-99169265ba894f1aa88386476ee3bbf5
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

Loading…