2,6-Difluoroaniline → HCID 54724198, compound

HRID 1866985Notes

Reaction equation

HRID 1866985 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[F:10][C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:12]=1[NH2:13]>O>[F:10][C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:12]=1[N:13]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 796472,6-DifluoroanilineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724198HCID 54724198, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (10.0 g, 0.079 mol) and 2,6 difluoroaniline (9.5 g, 0.073 mol) was heated at 170° C. under argon atmosphere for 20 min. The water formed was removed using a Dean-stark apparatus. The melt was cooled, the dark solid was tritutrated with EtOAc., and filtered. This material was washed thoroughly with EtOAc to afford the desired product 1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one 6.5 g (35%) as a light brown solid: 1H NMR (CD3OD/400 MHz) δ7.56 (m, 1H), 7.19 (m, 2H), 6.09 (m, 1H), 5.77 (d, 1H, J=2.4 Hz), and 1.99 (s, 3H); ES-HRMS m/z 238.0679 (M+H C12H10NO2F2 requires 238.0674).

Workup

  1. customwas removed
  2. temperatureThe melt was cooled
  3. filtration, and filtered
  4. washThis material was washed thoroughly with EtOAc

Sources & evidence

ORD record
ord-b79e2ad0e975478680bbcb1d4fecdd42
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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