Dimethylformamide → Methyl 3-(4-fluorophenethyl)-6-hydroxypyridin-2-carboxylate

HRID 1251921Notes

Reaction equation

HRID 1251921 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[C:9]([C:15]([O:17][CH3:18])=[O:16])=[N+:10]([O-])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.CN(C=[O:25])C>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[C:9]([C:15]([O:17][CH3:18])=[O:16])=[N:10][C:11]([OH:25])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 183244604-Fluorophenethyl-2-(methoxycarbonyl)pyridine-1-oxide

Product 1

HCID 178499128Methyl 3-(4-fluorophenethyl)-6-hydroxypyridin-2-carboxylate

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

A solution of 3-(4-fluorophenethyl)-2-(methoxycarbonyl)pyridine-1-oxide (7.96 g) in DMF (100 ml) and trifluoroacetic anhydride (40.9 ml) was stirred under an inert atmosphere at ambient temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, diluted with saturated aqueous sodium bicarbonate (150 ml) and extracted with dichloromethane (3×100 ml). The combined organic extracts were dried and concentrated under reduced pressure and the residue purified on a silica flash column eluting with methanol/dichloromethane (1:9) to give methyl 3-(4-fluorophenethyl)-6-hydroxypyridin-2-carboxylate as a cream solid (7.7 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium bicarbonate (150 ml)
  3. extractionextracted with dichloromethane (3×100 ml)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customthe residue purified on a silica flash column
  7. washeluting with methanol/dichloromethane (1:9)

Sources & evidence

ORD record
ord-cffeb43acb2444b8b09cebe752006caa
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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