Dimethylformamide → 4-Methyl-3,4-dihydro-2H-1,4-benzoxazine-7-carbaldehyde

HRID 2261079Notes

Reaction equation

HRID 2261079 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1.O=P(Cl)(Cl)Cl.CN([CH:20]=[O:21])C>O>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH:20]=[O:21])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 37550242H-1,4-Benzoxazine, 3,4-dihydro-4-methyl-

Product 1

HCID 27764044-Methyl-3,4-dihydro-2H-1,4-benzoxazine-7-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine dissolved in 200 ul DMF under Argon. POCl3 was added under Argon. The reaction was heated and a closed vial at 90° C. for 75 min. 1 ml of NaAc in water was added and stirred while a brown oil was formed. The oil was extracted with DCM. The organic layer was washed with brine, dried and evaporated to dryness, affording 0.18 g (76%) of 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine-7-carbaldehyde as colourless solid.

Workup

  1. temperatureThe reaction was heated
  2. customwas formed
  3. extractionThe oil was extracted with DCM
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bc2c738d7f7f48bd985ed56af1b0bd33
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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