Methanol → (2-Amino-5-fluoro-4-methoxyphenyl)(2-chlorophenyl)methanone

HRID 2112486Notes

Reaction equation

HRID 2112486 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:11].[CH3:19][OH:20].C[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([O:20][CH3:19])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 57642358(2-Amino-4,5-difluorophenyl)(2-chlorophenyl)methanone

Product 1

HCID 44182528(2-Amino-5-fluoro-4-methoxyphenyl)(2-chlorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.01 g (0.0075 mole) of (2-amino-4,5-difluorophenyl)-(2-chlorophenyl)-methanone (Xmm), 24 mL of methanol and 2.08 mL of 25% sodium methoxide solution was heated to reflux under an inert atmosphere for 80 minutes. The mixture was then cooled, taken up in ethyl acetate and washed twice with brine. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 2.04 g of aminobenzopheneone (2-amino-5-fluoro-4-methoxyphenyl)-(2-chlorophenyl)-methanone (Xa) as a crystalline yellow solid. MH+/Z=280.

Workup

  1. temperatureto reflux under an inert atmosphere for 80 minutes
  2. temperatureThe mixture was then cooled
  3. washwashed twice with brine
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e12b09c23204f6a942facbbdc75f623
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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