p-Toluenesulfonic acid → HCID 13469493, compound

HRID 894698Notes

Reaction equation

HRID 894698 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH2:25]O)=[C:5]([C:20]([O:22]CC)=[O:21])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[CH2:25][O:22][C:20](=[O:21])[C:5]=2[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13388338HCID 13388338, compound

Product 1

HCID 13469493HCID 13469493, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl 2-methyl-4-(2-chlorophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (592.5 mg) and p-toluenesulfonic acid (catalytic amount) in ethanol (6 ml) was refluxed for 4 hours. After the resultant solution was concentrated, diethyl ether was added to the residue. The precipitating crystals were collected by filtration to give ethyl 2-methyl-4-(2-chlorophenyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate (317.5 mg). The crude product was recrystallized from ethyl acetate to give colorless granules (210.3 mg), m.p. 211° to 212° C.

Workup

  1. concentrationAfter the resultant solution was concentrated
  2. additiondiethyl ether was added to the residue
  3. filtrationThe precipitating crystals were collected by filtration

Sources & evidence

ORD record
ord-41c44f2811b54d338233e201102a4bcb
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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