Chloroform → 4-(3-Methoxyphenyl)-1,3-dimethylpyridin-2(1H)-one

HRID 67799Notes

Reaction equation

HRID 67799 reaction equation
COC(C[C:6]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:11][CH2:10][N:9]([CH3:12])[C:8](=[O:13])[C:7]1=[CH2:14])=O.[OH-].[K+].CO.O.C(Cl)(Cl)Cl>CO.O>[CH3:12][N:9]1[CH:10]=[CH:11][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([CH3:14])[C:8]1=[O:13]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 14797Potassium HydroxideHCID 129475534-Methoxycarbonylmethyl-4-(3'-methoxyphenyl)-1-methyl-3-methylene-2-piperidoneHCID 22242641Methanol--water (1/1)

Product 1

HCID 204685844-(3-Methoxyphenyl)-1,3-dimethylpyridin-2(1H)-oneYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl ester 28 of Example 10 (1.20 g, 3.97 mmol) dissolved in CH3OH (5 mL, 0° C.) was rapidly added KOH (775 mg, 11.9 mmol) in 5 mL of 1/1 CH3OH/H2O. After 20 h at 25° C., CHCl3 (20 mL) and H2O (20 mL) were added, the separated aqueous layer was extracted with CHCl3 (20 mL) and the combined organic phases were dried and evaporated to give 178 mg (20%) of 1,3-dimethyl-4-(3'-methoxyphenyl)-2-pyridone (this arises from unreacted allylic alcohol under the alkaline hydrolysis conditions): NMR δ7.20 (m, 2H), 6.86 (m, 3H), 6.07 (d,J=7 Hz, 1H), 3.81 (s, 3H), 3.57 (s, 3H), 2.10 (s, 3H): IR (neat) 1640 cm-1 (broad); mass spectrum m/e (rel intensity) 229 (63), 228 (100). Anal. Calcd for C14H15NO2 : C, 73.3; H, 6.6; N, 6.1. Found: C, 73.0; H, 6.6; N, 6.1.

Workup

  1. extractionthe separated aqueous layer was extracted with CHCl3 (20 mL)
  2. customthe combined organic phases were dried
  3. customevaporated

Sources & evidence

ORD record
ord-13acf0ae5a84445ebc9c6039aafb7b86
Source dataset
uspto-grants-1982_08
Patent number
US04346224

Reaction notes

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