Nitric Acid → HCID 23433496, compound

HRID 1954568Notes

Reaction equation

HRID 1954568 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][C:2]([CH3:12])([CH3:1])[CH2:3][NH:4]2)=[CH:9][CH:8]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 138366683,3-Dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 23433496HCID 23433496, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydro-3,3-dimethylquinoline (51 mg, 0.32 mmol) was dissolved in sulfuric acid (0.5 mL) and the temperature lowered to 0° C. To this solution 90% fuming nitric acid (14 mL, 0.32 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 39 mg (58%) of 7-nitro-1,2,3,4-tetrahydro-3,3-dimethylquinoline. Data for 7-nitro-1,2,3,4-tetrahydro-3,3-dimethylquinoline: 1H NMR (400 MHz, CDCl3) 7.40 (dd, J=8.3, 2.1 1 H), 7.29 (d, J=1.8, 1 H), 7.01 (d, J=8.3 H, 1 H), 4.25 (s, 1 H), 2.98 (s, 2 H), 2.54 (s, 2 H), 1.01 (s, 6 H).

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-8d1b80951aea4a6fa52b87f5568a2236
Source dataset
uspto-grants-2000_09
Patent number
US06121450

Reaction notes

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