2-Amino-4-methylphenol → 2,6-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 635792Notes

Reaction equation

HRID 635792 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+]>C1(C)C=CC=CC=1>[CH3:7][CH:2]1[C:3](=[O:9])[NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[O:9]1

Participants

4

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 24758Sodium hydride

Product 1

HCID 40543662,6-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.39 g of 2-amino-4-methylphenol is mixed in 12 ml of toluene with 1.8 g of sodium hydride, and 3.95 ml of 2-bromo-propionic acid ethyl ether is added drop by drop at ice bath temperature. After 4 hours at room temperature, it is poured onto water, extracted with ethyl acetate, washed with brine, the organic phase is dried with magnesium sulfate and concentrated by evaporation. Column chromatography with hexane/ethyl acetate yields 43% product.

Workup

  1. additionis added drop by drop at ice bath temperature
  2. additionit is poured onto water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a9d098079e2a4a9f9dca53e5d7ae2f56
Source dataset
uspto-grants-2001_02
Patent number
US06191127B1

Reaction notes

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