Sulfuric Acid → 4-(5-Chloropyridin-2-yl)cyclohex-3-enecarboxylic acid

HRID 1174720Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=2)(O)[CH2:8][CH2:7]1)=[O:5])C.S(=O)(=O)(O)O>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH:8]=2)=[N:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(5-chloropyridin-2-yl)-4-hydroxycyclohexanecarboxylic acid ethyl ester (1.6 g) and sulfuric acid (5 ml) is heated at 60° C. for 15 minutes. After addition of water (0.4 ml) the mixture is again heated at 60° C. for 20 minutes. The cooled reaction mixture was diluted with water and washed with dichloromethane. The aqueous phase was adjusted to pH 7 with sodium bicarbonate solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 237.69 (C12H12ClNO2); MS (ESI): 238 (M+H+) was obtained in this way.

Workup

temperatureis again heated at 60° C. for 20 minutes
customThe cooled reaction mixture
washwashed with dichloromethane
extractionextracted with dichloromethane
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated
customMS (ESI): 238 (M+H+) was obtained in this way

Sources & evidence

ORD record: ord-fc68b2520565457ca075498e22057d91
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838547B2

Reaction notes

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