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

HRID 1472530Notes

Reaction equation

HRID 1472530 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-3d2e09f00f2c4adeb143b79d68033e15
Source dataset
uspto-grants-2015_04
Patent number
US09012479B2

Reaction notes

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