Pyridine → HCID 10197859, compound

HRID 2066385Notes

Reaction equation

HRID 2066385 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[NH4+]>C(Cl)Cl>[C:16]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5146Salicyl AlcoholHCID 6367Acetyl chlorideHCID 25517Ammonium Chloride

Product 1

HCID 10197859HCID 10197859, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Hydroxybenzyl alcohol (1.0 g) was dissolved in methylene chloride (20 ml), the solution was slowly added dropwise with pyridine (0.65 ml) and acetyl chloride (0.57 ml) under ice cooling, and the mixture was stirred for 30 minutes. The reaction mixture was added with saturated aqueous ammonium chloride, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (1.22 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8c87a3e42b594a11b09c2bbf8f5fd503
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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