Dimethylformamide → HCID 22254460, compound

HRID 434007Notes

Reaction equation

HRID 434007 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:9]=[C:8]1[CH3:21])(=[O:3])[CH3:2].CN(C)C=O.P(Cl)(Cl)([Cl:29])=O>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([Cl:29])[C:10]=2[N:9]=[C:8]1[CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 22254532HCID 22254532, compound

Product 1

HCID 22254460HCID 22254460, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A dried round bottom flask was charged with a stir bar, 2-(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethyl acetate (8.7 g, 30.49 mmol), anhydrous dimethylformamide (80 mL), and anhydrous toluene (100 mL) under nitrogen. To this brown mixture was added phosphorus oxychloride (3.1 mL) by syringe at ambient temperature. The reaction solution cleared in a couple of minutes and a slight exotherm was observed. The reaction was judged to be complete after 30 minutes. The volatiles were removed under reduced pressure. The resulting brown solid was partitioned between dichloromethane and 4% aqueous sodium bicarbonate to a pH of 8. The aqueous layer was extracted with dichloromethane (5×). The organic fractions were combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure and dried overnight at ambient temperature under reduced pressure to provide 9.2 g of 2-(4-chloro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl acetate as a brown oil.

Workup

  1. additionA dried round bottom flask was charged with a stir bar
  2. waitThe reaction solution cleared in a couple of minutes
  3. customThe volatiles were removed under reduced pressure
  4. customThe resulting brown solid was partitioned between dichloromethane and 4% aqueous sodium bicarbonate to a pH of 8
  5. extractionThe aqueous layer was extracted with dichloromethane (5×)
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customdried overnight at ambient temperature under reduced pressure

Sources & evidence

ORD record
ord-aa2b3b95df72411cb76a3e4fa311d8cd
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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