m-Chloroperbenzoic acid → 4-(5-(Carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide

HRID 592186Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([OH:18])=[O:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>ClCCl.CO>[C:16]([CH2:15][C:11]1[CH:12]=[C:13]([CH3:14])[C:8]([C:6]2[CH:5]=[CH:4][N+:3]([O-:27])=[C:2]([CH3:1])[CH:7]=2)=[N:9][CH:10]=1)([OH:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(2′,3-dimethyl-2,4′-bipyridin-5-yl)acetic acid 156-5 (100 mg, 0.41 mmol) in dichloromethane (3 mL) and methanol (0.5 mL) was added mCPBA (91 mg, 0.41 mmol) in small portions at 0° C. The mixture was stirred for 3 hours at 0° C., and then was concentrated to dryness to give 4-(5-(carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide 156-6 as white solid, which was used for next step without further purification. MS m/z 259.1 (M+1).

Workup

concentrationwas concentrated to dryness

Sources & evidence

ORD record: ord-fc331bf3077745279c114f1659f8744d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238646B2

Reaction notes

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