Water → 3-Methyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 1515072Notes

Reaction equation

HRID 1515072 reaction equation
[H][H].[N+:3]([C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10](=O)[CH3:11])([O-])=O.O.[N+](C(OC1C=CC=CC=1)C(=O)C)([O-])=O>CO>[CH3:11][CH:10]1[NH:3][C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[O:8][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 792392-Propanone, 1-(2-nitrophenoxy)-HCID 86645093NitrophenoxyacetoneHCID 178418361HCID 178418361, compound

Product 1

HCID 27637603-Methyl-3,4-dihydro-2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Reaction conditions: 150 bar of hydrogen, reaction temperature 80° C. with a residence time of about 60-90 minutes. The space velocity was about 2 g of o-nitrophenoxyacetone per g of catalyst used and hour. The catalyst used was a sponge metal catalyst from H. C. Starck, Amperkat Ni—Mo 3706 (exchange of the water under which the catalyst is stored for methanol). The yield was 90%; 42 g of nitrophenoxyacetone were converted per gram of theoretically dry catalyst. Thereafter, the hydrogenation had to be stopped owing to the massive formation of secondary components (in particular of the 3MBM dimer). Good mixing was ensured by stirring. In order to prevent precipitation of the reactant solution, it was heated to 40° C.

Workup

  1. customReaction conditions
  2. waitused and hour
  3. additionGood mixing
  4. customprecipitation of the reactant solution, it

Sources & evidence

ORD record
ord-54d56c0d9b33462987f5a633cd8612e1
Source dataset
uspto-grants-2012_07
Patent number
US08222408B2

Reaction notes

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