Nitric Acid → HCID 23433508, compound

HRID 1938491Notes

Reaction equation

HRID 1938491 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][CH:2]([CH3:1])[CH2:3][NH:4]2)=[CH:9][CH:8]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5902243-Methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 23433508HCID 23433508, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydro-3-methylquinoline (51 mg, 0.35 mmol) was dissolved in sulfuric acid (0.5 mL) and the temperature lowered to 0° C. To this solution 90% fuming nitric acid (15 mL, 0.35 mmol) was added slowly and the mixture stirred at 0° C. for 1 h, then warmed to rt. The reaction mixture was then poured onto 1 g of ice and extracted with dichloromethane (2×5 mL). The organic phase was washed with saturated aqueous NaHCO3 (3 mL) and concentrated in vacuo to a reddish residue that was subjected to chromatography (silica gel, hexanes/ethyl acetate, 85:15) which afforded 8.2 mg (12%) of 7-nitro-1,2,3,4-tetrahydro-3-methylquinoline. Data for 7-nitro-1,2,3,4-tetrahydro-3-methylquinoline: 1H NMR (400 MHz, CDCl3) 7.39 (dd, J=8.25, 2.2, 1H), 7.27 (d, J=2.3, 1H), 7.01 (d, J=8.3, 1H), 4.19 (s, 1H), 3.33 (m, 1H), 2.94 (dd, J=10.1, 10.1, 1H), 2.86 (ddd, J=13.8, 4.7, 1.7, 1H), 2.46 (dd, J=16.6, 10.0, 1H), 2.05 (m, 1H), 1.06 (d, J=6.7, 3H).

Workup

  1. customlowered 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 saturated aqueous NaHCO3 (3 mL)
  6. concentrationconcentrated in vacuo to a reddish residue that

Sources & evidence

ORD record
ord-9d5466514a434cf9ac8aa2d3a8c49c0c
Source dataset
uspto-grants-1997_12
Patent number
US05693647

Reaction notes

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