Methanol → Methyl 5-hydroxypyridine-2-carboxylate

HRID 1678061Notes

Reaction equation

HRID 1678061 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:11]N(C=O)C.C(Cl)(=O)C(Cl)=O.CO>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-hydroxypyridine-2-carboxylic acid (5.0 g, 36 mmol) suspended in CH2Cl2 (120 mL) was added DMF (1 mL) followed by oxalyl chloride (4.7 g, 37 mmol). After 1 hour, excess MeOH was added. The resulting mixture was stripped of solvent in vacuo yielding a brown solid that was washed with hot EtOAc. Yielded 4.6 g of product.

Workup

  1. customyielding a brown solid that
  2. washwas washed with hot EtOAc

Sources & evidence

ORD record
ord-4162643f60614b36ae71fbd7196b5e74
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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