Water → 2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

HRID 840374Notes

Reaction equation

HRID 840374 reaction equation
C([O:3][C:4](=O)[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2OCC[O:15]2)=[CH:10][C:9]=1[N+:19]([O-])=O)[CH3:6])C.O>C(O)(=O)C.[Fe]>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]2[O:7][CH:5]([CH3:6])[C:4](=[O:3])[NH:19][C:9]=2[CH:10]=1)=[O:15]

Participants

5

Reactant 2

HCID 962Water2×HCID 57232269HCID 57232269, compound

Product 1

HCID 218738872-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehydeYield 97.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

28.8 g of pulverized iron is added in portions to 34 g of 2-(4-(1,3-dioxolan-2-yl)-2-nitrophenoxy)propionic acid ethyl ester in 360 ml of glacial acetic acid with 80 ml of water while being cooled in an ice bath. The mixture is hot. After 2 hours, it is poured onto 1 l of water, extracted with ethyl acetate, and the organic phase is washed with brine. It is dried with magnesium sulfate and concentrated by evaporation. 20.3 g of brownish solid results.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with brine
  4. dry with materialIt is dried with magnesium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ed45fd133e4c4bba840060cc69578bfd
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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