Methyl4,6-dichloronicotinate → (4,6-Dichloropyridin-3-yl)methanol

HRID 1727080Notes

Reaction equation

HRID 1727080 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:11][C:12]1[C:17]([C:18](OC)=[O:19])=[CH:16][N:15]=[C:14]([Cl:22])[CH:13]=1>CCOCC>[Cl:11][C:12]1[CH:13]=[C:14]([Cl:22])[N:15]=[CH:16][C:17]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 2764083Methyl4,6-dichloronicotinateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 2762727(4,6-Dichloropyridin-3-yl)methanolYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminum hydride (2.4 g, 64 mmol) and aluminum chloride (17 g, 128 mmol) in Et2O (200 mL) at 0° C. was added a solution of methyl 4,6-dichloronicotinate (13.1 g, 64 mmol) in Et2O (100 mL) dropwise with stirring. The resulting solution was heated at reflux for one hour. The reaction mixture was quenched with 100 mL of H2O/ice. The resulting solution was extracted with EtOAc (2×500 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to afford 4.5 g (43%) of (4,6-dichloropyridin-3-yl)methanol.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for one hour
  3. customThe reaction mixture was quenched with 100 mL of H2O/ice
  4. extractionThe resulting solution was extracted with EtOAc (2×500 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea5fd62d1e134b71aa31521692b8a8a2
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

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