Methyl Nicotinate → HCID 18446610, compound

HRID 1269035Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[C:9](OC)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1>>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:16])[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7151Methyl Nicotinate

HCID 876016-Chloro-2-picoline

Product 1

HCID 18446610HCID 18446610, compound

Procedure

In a similar manner as described in Example 1 from 6-chloro-2-picoline (9.3 g, 73 mmol) and methyl nicotinate (10.0 g, 73 mmol), 2-(6-chloro-2-pyridinyl)-1-(3-pyridinyl)ethanone was obtained as a syrup. This syrup (10 g, 70 mmol) was treated with hydroxylamine hydrochloride (24.3 g, 350 mmol) followed by the addition of a sodium hydroxide solution (14 g, 350 mmol in 30 mL of water) as described in example 1 to give 2-(6-chloro-2-pyridinyl)-1-(3-pyridinyl)ethanone oxime (14.4 g, 80%) as a white solid. 1H NMR (CDCl3): δ 8.84 (d, 1H), 8.40 (dd, 1H), 8.00 (m, 1H), 7.50 (t, 1H), 7.2–7.4 (m, 3H), 4.26 (s, 2H); MS m/z 248 (M+1).

Sources & evidence

ORD record: ord-2d83481497804073a1ed8519eb6af93a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199120B2

Reaction notes

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