Pyridine → 3-Methylcarbonyloxyquinoline

HRID 863260

Reaction equation

HRID 863260 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.N1C=CC=CC=1.C(Cl)Cl>O>[CH3:2][C:1]([O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 113763-Hydroxyquinoline

Product 1

HCID 154938353-Methylcarbonyloxyquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.35 ml of acetyl chloride are added dropwise to a mixture of 2.5g of 3-hydroxyquinoline (prepared by the method described by Mills and Watson in J.Chem. Soc., 97, 753 (1910)), 8.6 ml of pyridine and 50 ml of methylene chloride, while cooling with ice. After the reaction mixture has been stirred at room temperature for 10 minutes, 50 ml of water are added. Customary working up and purification of the crude product by FC over 50 g of silica gel (mobile phase C) gives 3-methylcarbonyloxyquinoline: Rf (A)=0.55; IR (CH2Cl2): 1770(s) cm-1.

Workup

  1. customprepared by the method
  2. custompurification of the crude product by FC over 50 g of silica gel (mobile phase C)

Sources & evidence

ORD record
ord-6a16a314908e48289e1152442eec1cdc
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Linked notes

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