Water → 2-Methyl-6,7,8,9-tetrahydronaphth[2,3-b]-1,4-oxazin-3(4H)-one

HRID 840366Notes

Reaction equation

HRID 840366 reaction equation
O.C([O:4][C:5](=O)[CH:6]([O:8][C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=1)[CH3:7])C>C(O)(=O)C.[Fe]>[CH3:7][CH:6]1[O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:18]=2[NH:19][C:5]1=[O:4])[CH2:15][CH2:14][CH2:13][CH2:12]3

Participants

5

Reactant 2

HCID 962WaterHCID 179106822-(5,6,7,8-Tetrahydro-3-nitro-2-naphthoxy)-propionic acid ethyl ester

Product 1

HCID 97944102-Methyl-6,7,8,9-tetrahydronaphth[2,3-b]-1,4-oxazin-3(4H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

In a mixture of 10 ml of glacial acetic acid with 1.25 ml of water, 2-(5,6,7,8-tetrahydro-3-nitro-2-naphthoxy)-propionic acid ethyl ester is dissolved and mixed in portions with 960 mg of iron powder. It is heated, cooled and poured onto water. The crystals are suctioned off and washed with water, dissolved again with ethyl acetate and washed with soda solution, the organic phase is washed with brine, dried with magnesium sulfate and concentrated by evaporation. 740 mg, yield 81%, results.

Workup

  1. dissolutionis dissolved
  2. temperatureIt is heated
  3. temperaturecooled
  4. additionpoured onto water
  5. washwashed with water
  6. dissolutiondissolved again with ethyl acetate
  7. washwashed with soda solution
  8. washthe organic phase is washed with brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated by evaporation
  11. custom740 mg, yield 81%, results

Sources & evidence

ORD record
ord-f6530d0eb67b4a569b3c12c51ff8716b
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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