3-Pyridinemethanol → HCID 19833177, compound

HRID 1639381Notes

Reaction equation

HRID 1639381 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9])(=[O:3])[CH3:2].S(Cl)(Cl)=O.O[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>C(Cl)Cl>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][CH2:13][C:14]([O:16][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:15])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 24386Thionyl ChlorideHCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 19833177HCID 19833177, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.00 g (0.006 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 0.5 ml (0.006 mol) of thionyl chloride in 20 ml of methylene chloride are stirred at room temperature for 5 minutes and then a solution of 2.2 ml (0.023 mol) of 3-hydroxymethylpyridine in 20 ml of methylene chloride is added thereto at 0°. After stirring at room temperature for 1 hour, the solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on aluminum oxide with ethyl acetate gives 3-pyridylmethyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate as a beige oil.

Workup

  1. customat 0°
  2. concentrationthe solution is concentrated
  3. extractionextracted with methylene chloride/water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent is distilled in a vacuum

Sources & evidence

ORD record
ord-4e46de76285b4170b3ad046243f94132
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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