Methylamine → 2-Amino-5-fluoro-N-methylbenzamide

HRID 62485

Reaction equation

HRID 62485 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10]C(=O)[O:8][C:7](=O)[C:6]=2[CH:13]=1.[CH3:14][NH2:15]>O1CCCC1>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:13][C:6]=1[C:7]([NH:15][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 2885605-Fluoroisatoic anhydride

Product 1

HCID 431325582-Amino-5-fluoro-N-methylbenzamideYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione (200 mg, 1.104 mmol) was dissolved in dry tetrahydrofuran (THF) (10 mL), at which time methyl amine (3.31 mL, 6.63 mmol) was added. The reaction was stirred at room temperature for 1 h, then concentrated under vacuum. The crude product was purified on silica (Biotage, 40% EtOAc/hexene) to afford the title compound (120 mg, 65%) as a white solid. LC-MS (ES) m/z=169.1 (M+H)+

Workup

  1. additionwas added
  2. concentrationconcentrated under vacuum
  3. customThe crude product was purified on silica (Biotage, 40% EtOAc/hexene)

Sources & evidence

ORD record
ord-aef9e4fc5a7a44e5a961eff5a775f7f9
Source dataset
uspto-grants-2016_09
Patent number
US09446034B2

Linked notes

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