Dimethylamine → 2-Dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridine

HRID 256163Notes

Reaction equation

HRID 256163 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([F:9])=[C:7](F)[N:6]=[C:5]([F:11])[C:4]=1[F:12].[CH3:13][NH:14][CH3:15].O>C(O)C>[CH3:13][N:14]([CH3:15])[C:7]1[C:8]([F:9])=[C:3]([CH2:2][OH:1])[C:4]([F:12])=[C:5]([F:11])[N:6]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 139851584-Hydroxymethyl-2,3,5,6-tetrafluoropyridine

Product 1

HCID 139851642-Dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridineYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.0 g (0.0055 mole) of 4-hydroxymethyl-2,3,5,6-tetrafluoropyridine (from Example 5) and 0.23 g (0.0050 mole) of dimethylamine in 25 ml of ethanol was refluxed for approximately twenty hours. The reaction mixture was cooled and was poured into water. This mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure, yielding 0.9 g of 2-dimethylamino-4-hydroxymethyl-3,5,6-trifluoropyridine as a yellow oil. The structure and nmr spectra are set forth in Table 1C below.

Workup

  1. temperaturewas refluxed for approximately twenty hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThis mixture was extracted with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-441e0d58445b4beaa592252f1f6fb227
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Reaction notes

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