Sodium Hydroxide → HCID 59326817, compound

HRID 1880116Notes

Reaction equation

[NH2:1][O:2]S(O)(=O)=O.[F:7][C:8]1[C:13]([CH:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)=[CH:12][CH:11]=[CH:10][N:9]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)=O.C(OCC)(=O)C>[F:7][C:8]1[C:13]([CH:14]2[CH2:19][CH2:18][C:17](=[N:1][OH:2])[CH2:16][CH2:15]2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of aminooxysulfonic acid (0.35 g, 3.11 mmol) in 96% formic acid (2.5 mL) was added dropwise to a solution of 4-(2-fluoropyridin-3-yl)cyclohexanone (0.50 g, 2.59 mmol) in 96% formic acid (2.5 mL) at room temperature. The solution was stirred for 15 min, then warmed to 40° C. for 2 h, then cooled 0° C. Ethyl acetate (10 mL) was added and the mixture was neutralized by the dropwise addition of 10 N aqueous sodium hydroxide solution (10 mL) followed by saturated aqueous sodium bicarbonate. The resulting biphasic mixture was separated, the aqueous layer was extracted with ethyl acetate (2×), and the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 4-(2-fluoropyridin-3-yl)cyclohexanone oxime. [M+1]=209.1.

Workup

temperaturecooled 0° C
customThe resulting biphasic mixture was separated
extractionthe aqueous layer was extracted with ethyl acetate (2×)
dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record: ord-1480d890789542de9f999b4384ed1485
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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