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

HRID 2043104Notes

Reaction equation

HRID 2043104 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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 684258024-(5-Chloropyridin-2-yl)-4-hydroxycyclohexanecarboxylic acid ethyl ester

Product 1

HCID 684282604-(5-Chloropyridin-2-yl)cyclohex-3-enecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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

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

Sources & evidence

ORD record
ord-0eb6dd03ec3c440e9209fef0254dfdb6
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

Loading…