Nitric Acid → HCID 70819396, compound

HRID 512092Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:21]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])[NH:23][C:22]=1[CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH2:5]([C:21]1[C:26](=[O:27])[C:25]([N+:1]([O-:4])=[O:2])=[C:24]([CH3:28])[NH:23][C:22]=1[CH3:29])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

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 4 (58 mg) in sulphuric acid (d 1.64, 0.5 g). The reaction 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 reaction 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-hexadecyl-2,6-dimethyl-5-nitropyridin-4(1H)-one (14) as a yellow oil: yield 41 mg (62%); silica gel TLC Rf 0.60 (1:1 hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 0.82-0.85 (m, 3H), 1.21-1.29 (m, 28H), 2.33 (s, 3H), 2.39 (s, 3H) and 2.46-2.52 (m, 2H).

Workup

temperaturethen cooled
additionadded to ice
extractionThe reaction mixture was extracted with portions of ethyl ether
dry with materialThe combined organic phase was dried over anhydrous MgSO4
concentrationconcentrated under diminished pressure
customto afford
washa crude residue Elution with hexane/ethyl acetate

Sources & evidence

ORD record: ord-87ba3d84ffc54beeab115579dde3ae39
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102626B2

Reaction notes

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