Diethyl Ether → 40472-76-2

HRID 2086258Notes

Reaction equation

HRID 2086258 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6](C(O)=O)[CH:5]=1.C([O:15][CH2:16][CH3:17])C>[Cl-].[NH4+]>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:16]([OH:15])([CH3:17])[CH3:1])[CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether4×HCID 2308904-Chloropyridine-2-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 2272721740472-76-2

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A 1.5 M solution of methyllithium in diethyl ether (6.0 ml) dissolved in diethyl ether (15 ml) was treated dropwise with a solution of 4-chloropyridine-2-carboxylic acid in diethyl ether (15 ml) under an argon atmosphere, and stirred at room temperature for 2 hours. The reaction mixture was diluted with a saturated solution of ammonium chloride and diethyl ether, and the organic phase was washed with brine, dried and concentrated. The resultant residue was purified by a column chromatography on a silica gel (ethyl acetate:methanol=20:1) to obtain the title compound (459 mg) as a tan oil.

Workup

  1. washthe organic phase was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe resultant residue was purified by a column chromatography on a silica gel (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-ef698c8b2d8b41c78f5165e266ccdca9
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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