Dimethylformamide → HCID 21947071, compound

HRID 2214337Notes

Reaction equation

HRID 2214337 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[C:6]([CH3:14])=[CH:5][C:4]1([CH3:16])[CH3:15])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:25]=[O:26])C>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:25]=[O:26])=[C:10]([OH:13])[CH:11]=2)[C:6]([CH3:14])=[CH:5][C:4]1([CH3:15])[CH3:16])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 154511031-Ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-ol

Product 1

HCID 21947071HCID 21947071, compound

Procedure

To a 100 ml flask, 1.0 g (4.60 mmol) of Compound 4 30.0 ml of dry DMF and 0.76 g (5.00 mmol) of POCl3 were added, and the mixture was stirred at room temperature for 24 hours under nitrogen gas flow. After evaporation of the solvent under reduced pressure, the reaction mixture was dissolved in ethyl acetate and then washed with water. The resultant was dried over anhydrous sodium sulfate and the residue was purified by column chromatography (SiO2, n-hexane:ethyl acetate=1:1) to obtain the desired product.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. dissolutionthe reaction mixture was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe resultant was dried over anhydrous sodium sulfate
  5. customthe residue was purified by column chromatography (SiO2, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-73396456469d481494e7008f3a2f09bb
Source dataset
uspto-grants-2006_09
Patent number
US07109043B2

Reaction notes

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