Dimethylformamide → HCID 22008947, compound

HRID 322011Notes

Reaction equation

HRID 322011 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]([OH:12])[C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[H-].[Na+].CN(C=O)C.[CH3:21][CH2:22][CH2:23]Br>O>[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]([O:12][CH2:21][CH2:22][CH3:23])[C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 2916143-methoxy-2-methyl-6-nitrophenol

Product 1

HCID 22008947HCID 22008947, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (10.93 mmol) of 3-methoxy-2-methyl-6-nitrophenol (prepared according to R. A. Raphael, P. Ravenscoft, J. Chem. Soc. Perkin Trans. I, (1988), 1823-1828) were added in portions under an argon atmosphere to a suspension of 525 mg (1 2.02 mmol) of NaH in 30 ml of abs. DMF cooled to 0° C. After stirring at 0° C. for 30 min, 1.17 ml (12.70 mmol) of n-propyl bromide were added dropwise. The reaction solution was stirred at 70° C. for 8 h. Subsequently, 70 ml of H2O were added with ice cooling, and the mixture was then concentrated to dryness. The residue was taken up in EA, and the solution was washed 3× with H2O, dried over Na2SO4, and concentrated. Drying in a high vacuum afforded 2.37 g of the title compound in the form of a brown oil.

Workup

  1. stirringThe reaction solution was stirred at 70° C. for 8 h
  2. concentrationthe mixture was then concentrated to dryness
  3. washthe solution was washed 3× with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customDrying in a high vacuum

Sources & evidence

ORD record
ord-da0baa525a394121a79bce5a06bc5b2c
Source dataset
uspto-grants-2001_04
Patent number
US06211196B1

Reaction notes

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