Methylamine → 2-amino-4-fluoro-N-methylbenzamide

HRID 1362868Notes

Reaction equation

HRID 1362868 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=O)[O:7]C(=O)[NH:9][C:4]=2[CH:3]=1.[CH3:14][NH2:15]>>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:13]=[CH:12][C:5]=1[C:6]([NH:15][CH3:14])=[O:7]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 569516612-amino-4-fluoro-N-methylbenzamideYield 62%

Conditions

Temperature
110 °C

Procedure

A microwave vial was charged with 7-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione (750 mg, 4.14 mmol) and methyl amine 40% aqueous solution (19.8 mL, 22.8 mmol, 5.5 eq). The reaction was stirred and heated in the microwave for 6 min at 110° C. The aqueous solution was extracted with methylene chloride (3×). Organic layers were combined and washed with 5% NaHCO3 solution and brine, dried over sodium sulfate, then concentrated to give a pale yellow oil that was used without further purification (434 mg, 62% yield). MS: M(C8H9FN2O)=168.17, (M+H)+=169 and (M+H−NHMe)+=138.

Workup

  1. extractionThe aqueous solution was extracted with methylene chloride (3×)
  2. washwashed with 5% NaHCO3 solution and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a pale yellow oil that
  6. customwas used without further purification (434 mg, 62% yield)

Sources & evidence

ORD record
ord-4bde32452d6b4ac2b783fe43ec69d784
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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