Sulfuric Acid → 6-(2-Aminoethyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 840375Notes

Reaction equation

HRID 840375 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH:13]=[CH:14][N+:15]([O-])=O)[CH:11]=[CH:12][C:4]=2[O:3]1.S(=O)(=O)(O)O>[Pt](=O)=O.C(O)(=O)C>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][CH2:14][NH2:15])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 54562509HCID 54562509, compound

Product 1

HCID 226231216-(2-Aminoethyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-oneYield 52.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

2 g (8.5 mmol) of 2-methyl-3-oxo-6-(2-nitro-ethenyl)-3,4-dihydro-2H-1,4-benzoxazine is mixed with 80 ml of acetic acid and 1.6 ml of concentrated sulfuric acid and, after 200 mg of platinum dioxide is added, it is reduced in an autoclave. The catalyst is then suctioned off, and the batch is spun in until a dry state is reached. The remaining residue is chromatographed on silica gel (mobile solvent: isopropanol/ammonia). 923.5 mg (52.4%) of the described compound is obtained.

Workup

  1. customThe remaining residue is chromatographed on silica gel (mobile solvent: isopropanol/ammonia)

Sources & evidence

ORD record
ord-6e1e1810e5664fc9885352c48e5dcd44
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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