Sodium Nitrite → HCID 136335130, compound

HRID 1432422Notes

Reaction equation

[N:1]([O-:3])=O.[Na+].[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14](=[O:23])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[CH:13][C:8]=2[O:7][CH2:6]1>CC(O)=O.C1COCC1.O>[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14](=[O:23])[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:1][OH:3])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium nitrite (0.405 g, 5.88 mmol) was added to a solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone (1.0 g, 3.92 mmol; see Example 3B above) in a mixture of HOAc/THF/H2O (6:4:1, 22 mL). The mixture was stirred at 0° C. for 1 hour and then at room temperature for 1 hour. Solvent was removed under reduced pressure. Residue was dissolved in water and NaOH (3N) was added until the pH value was more than 8. The aqueous solution was then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 0.90 g (81%) of 1-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)ethane-1,2-dione 2-oxime as a yellow foam. MS (ESP+) m/z 285.1 (M+1). 1H NMR (300 MHz, CDCl3) δ 7.49 (m, 4H), 7.09 (d, 1H, J=7.5 Hz), 6.81 (d, 1H, J=7.8 Hz), 6.04 (s, 2H), 2.43 (s, 3H).

Workup

waitat room temperature for 1 hour
customSolvent was removed under reduced pressure
dissolutionResidue was dissolved in water
additionNaOH (3N) was added until the pH value
extractionThe aqueous solution was then extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-bd7bc32f912948f2ae6bd58fe880930a
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612094B2

Reaction notes

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