Sodium Carbonate → 7-Fluoro-3-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

HRID 548726Notes

Reaction equation

HRID 548726 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[C:13](=O)([O-])[O-].[Na+].[Na+]>C=O.C(O)=O>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:7])[N:8]([CH3:13])[CH2:9][O:12][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 576632174-Fluoro-2-hydroxy-N-methylbenzamide

Product 1

HCID 576631937-Fluoro-3-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

A mixture of 4-fluoro-2-hydroxy-N-methyl-benzamide (0.3 g, 1.77 mmol) in formaldehyde (37% aq. soln) (2 mL) and formic acid (2 mL) was refluxed for 1 hour then poured onto ice. The mixture was neutralised with sodium carbonate and extracted into chloroform (3×30 mL). The combined organics were dried (MgSO4), and reduced in vacuo to give a white solid which was chromatographed on silica, eluting with 10-50% ethyl acetate in isohexane to give the desired compound as a white solid (0.24 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. additionthen poured onto ice
  3. extractionextracted into chloroform (3×30 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. customto give a white solid which
  6. customwas chromatographed on silica
  7. washeluting with 10-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3a14f44bd2bd48a2a3cdf00f41c69cd9
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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