Nitric Acid → HCID 70819594, compound

HRID 1051146Notes

Reaction equation

HRID 1051146 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:12]1[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[NH:14][C:13]=1[CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH2:5]([C:12]1[C:17](=[O:18])[C:16]([N+:1]([O-:4])=[O:2])=[C:15]([CH3:19])[NH:14][C:13]=1[CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 70819321HCID 70819321, compound

Product 1

HCID 70819594HCID 70819594, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

Premixed nitric acid (d 1.5, 0.15 g) and sulfuric acid (0.05 g) was added dropwise at 5-10° C. to 3 (94 mg) in sulfuric acid (d 1.64, 0.5 g). The mixture was heated at 80° C. for 1 hr then cooled and added to ice. Saturated aqueous sodium carbonate was added until effervescence ceased. The mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. Elution with hexane/ethyl acetate gave 3-heptyl-2,6-dimethyl-5-nitropyridin-4(1H)-one (13) as a yellow oil: yield 76 mg (67%); silica gel TLC Rf 0.45 (1:1 hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 0.77-0.81 (m, 3H), 1.19-1.27 (m, 10H), 2.29 (s, 3H), 2.35 (s, 3H) and 2.44-2.47 (m, 2H).

Workup

  1. temperaturethen cooled
  2. additionadded to ice
  3. extractionThe mixture was extracted with portions of ethyl ether
  4. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated under diminished pressure
  6. customto afford a crude residue
  7. washElution with hexane/ethyl acetate

Sources & evidence

ORD record
ord-dc7efc2834344afa8d1e68c74742f19a
Source dataset
uspto-grants-2016_07
Patent number
US09388163B2

Reaction notes

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