Methylamine → 2-amino-6-fluoro-N-methylbenzamide

HRID 1362866Notes

Reaction equation

HRID 1362866 reaction equation
[F:1][C:2]1[C:7]2[C:8](=O)[O:9]C(=O)[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:14][NH2:15]>O>[NH2:11][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:7]=1[C:8]([NH:15][CH3:14])=[O:9]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27830576-Fluoroisatoic anhydride

Product 1

HCID 208067942-amino-6-fluoro-N-methylbenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottomed flask was charged with 5-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione (500 mg, 2.8 mmol) and 30 mL water. The reaction was stirred for 15 min and then methylamine was added. The reaction was then stirred for 2 h. It was then extracted three times with ethyl acetate. Organic layers were combined and dried over sodium sulfate, then concentrated. The product was identified as 2-amino-6-fluoro-N-methylbenzamide (365 mg, 2.4 mmol, 86% yield). MS: M(C8H9FN2O)=168.17, (M+H)+=169.3.

Workup

  1. stirringThe reaction was then stirred for 2 h
  2. extractionIt was then extracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-30e8055cdfb144e7a81cff65ca22c0b3
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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