2-Chloronicotinic acid → (2-Chloropyridin-3-yl)methanol

HRID 1598955Notes

Reaction equation

HRID 1598955 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanolYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-chloronicotinic acid (10.0 g, 63.4 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added lithium aluminum hydride (63 mL of a 1.0M solution in THF, 63 mmol) over 10 minutes. The solution was allowed to warm to room temperature over 2 h. Small quantities of ice were carefully added to quench the reaction followed by water. The aqueous solution was extracted with ether. The combined organic extracts were washed with water and saturated aqueous NaCl, dried over MgSO4, and concentrated in vacuo to give the title compound of Step A as an orange solid (6.18 g). 1H NMR (CDCl3, 300 MHz) δ8.30 (dd, 1H), 7.90 (dd, 1H), 7.29 (dd, 1H), 4.80 (s,2H), 2.42 (br s,1H).

Workup

  1. additionSmall quantities of ice were carefully added
  2. customto quench the reaction
  3. extractionThe aqueous solution was extracted with ether
  4. washThe combined organic extracts were washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5b51e046da9425a9533f7357b5d7480
Source dataset
uspto-grants-1998_04
Patent number
US05739326

Reaction notes

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