p-Toluenesulfonic acid → HCID 71623010, compound

HRID 1471679Notes

Reaction equation

HRID 1471679 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[OH:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[N:5]1[CH:6]=[CH:7][CH:2]=[C:3]([CH2:8][O:9][C:17]2[C:12]([CH:11]=[O:10])=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 75103-PyridinemethanolHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 71623010HCID 71623010, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-chloro-3-pyridine aldehyde (1.0 g, 7 mmol, 1.0 eq), 3-hydroxymethylpyridine (5.4 g, 49.45 mmol, 7 eq) and p-toluenesulfonic acid mon hydrate (1.3 g, 7.0 mmol, 1.0 eq) in benzene (30 mL) were heated using a Dean-Stark trap for 24 h. Solvent was removed and purified by column chromatography to provide the alkylation product. MS: exact mass calculated for C12H1N2O2, 214.22; m/z found, 215 [M+H]+.

Workup

  1. customfor 24 h
  2. customSolvent was removed
  3. custompurified by column chromatography
  4. customto provide the alkylation product

Sources & evidence

ORD record
ord-4377d68c31094d9c918de2f5cc92f75b
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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