Dimethylformamide → 5-Methoxypicolinoyl chloride

HRID 1995846Notes

Reaction equation

HRID 1995846 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1.CN(C=O)C.S(Cl)([Cl:19])=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([Cl:19])=[O:11])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 119589395-Methoxypyridine-2-carboxylic acid

Product 1

HCID 450814415-Methoxypicolinoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-methoxy-2-pyridylcarboxylic acid (11.9 g, 77.5 mmol) and DMF (5.4 ml, 69 mmol) in 200 ml of tetrahydrofuran (THF) at 5° is added thionyl chloride (8.4 ml, 116 mmol) over 15 minutes. After addition, the slurry is allowed to warm slowly to RT. After 3 hours, the reaction is rotoevaporated to give 5-methoxy-2-pyridylcarboxylic acid chloride. This acid chloride is gradually added, with cooling, to rapidly stirring ammonium hydroxide (40 ml, 340 mmol), and the slurry is stirred for 1 hour. The reaction is filtered and the residue is dried. To this is added dry toluene, with stirring, followed by filtration. More toluene is added, followed by rotoevaporation to give 5-methoxy-2-pyridylcarboxamide.

Workup

  1. additionAfter addition

Sources & evidence

ORD record
ord-e646f91311864679a0019436bb8c880f
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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