Methylamine → HCID 57742969, compound

HRID 553531Notes

Reaction equation

HRID 553531 reaction equation
[F:1][C:2]1[C:3]([NH:13][CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7]C)=O.FC1C(F)=C(F)C=C[C:17]=1[C:18](OC)=[O:19].[C:28](=[O:31])([O-])[O-:29].[K+].[K+].CN.[CH2:36]1COC[CH2:37]1>CCOC(C)=O>[F:12][C:11]1[C:2]([F:1])=[C:3]2[C:4]([C:5]([OH:7])=[C:17]([C:28]([O:29][CH2:36][CH3:37])=[O:31])[C:18](=[O:19])[N:13]2[CH3:14])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2760117Methyl 2,3,4-trifluorobenzoateHCID 67408030HCID 67408030, compound

Product 1

HCID 57742969HCID 57742969, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
24 °C

Procedure

Methyl 3,4-difluoro-2-(methylamino)benzoate. A mixture of methyl 2,3,4-trifluorobenzoate (available from Oakwood Products, West Columbia, S.C.) (5.00 g, 26 mmol), and potassium carbonate (4.0 g, 29 mmol) was treated with 2M methylamine in THF (17 mL, 34 mmol), and stirred at 24° C. for 18 hours. The mixture was diluted with EtOAc, washed with water, dried over MgSO4, and evaporated. The crude product was purified by flash chromatography (EtOAc/hexanes) to give the title compound. MS (ESI) m/z: Calculated; 201.2: Observed; 202.1. 1H NMR (300 MHz, CDCl3) δ ppm 7.54-7.67 (1H, m), 6.26-6.43 (1H, m), 3.94 (1H, s), 3.84 (3H, s), 3.15 (3H, dd, J=6.8, 5.5 Hz).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-643999c9230743fca3c82a458febd0d5
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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