Methylamine → 2-amino-5-hydroxy-N-methylbenzamide

HRID 77397Notes

Reaction equation

HRID 77397 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6]C(=O)[O:8][C:9](=O)[C:4]=2[CH:3]=1.[CH3:14][NH2:15]>C(O)C>[NH2:6][C:5]1[CH:12]=[CH:13][C:2]([OH:1])=[CH:3][C:4]=1[C:9]([NH:15][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 699296892-amino-5-hydroxy-N-methylbenzamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione (500 mg, 2.79 mmol) in ethanol (20 mL) was cooled to 0° C. and methylamine solution (33% in ethanol, 2.92 mL, 27.9 mmol) added and the reaction stirred for 3 days. The solvent was removed under reduced pressure and the product purified by silica chromatography, eluent 5% methanol in dichloromethane to yield 2-amino-5-hydroxy-N-methylbenzamide (280 mg, 1.68 mmol).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product purified by silica chromatography, eluent 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7e3f3c855ab1489c911eff32193937b9
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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