Dimethylcarbamoyl Chloride → 3-(N,N-dimethylcarbamoyl)-2-isopropylpyrazolo[1,5-a]pyridine

HRID 839798Notes

Reaction equation

HRID 839798 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:13][N:14]([CH3:18])[C:15]([C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)=[O:16]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 203220123-(N,N-dimethylcarbamoyl)-2-isopropylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A mixture of 1.6g of 2-isopropylpyrazolo[1,5-a]pyridine and 2.1g of N,N-dimethylcarbamoyl chloride was dissolved in 20 ml of nitrobenzene. Four grams of aluminum chloride (powder) was added at room-temperature to the resulting solution and reaction mixture was refluxed for 8 hr and concentrated under reduced pressure. Water was added to the residue and the mixture was made basic with potassium hydroxide solution, extracted with chloroform. The chloroform solution was dried over sodium sulfate and concentrated. The residue was column chromatographed over alumina to give objective product. Distillation gave colorless oil, bp 175° (2 mmHg). Yield 1.1g (50%).

Workup

  1. temperaturewas refluxed for 8 hr
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed over alumina
  8. customto give objective product
  9. distillationDistillation
  10. customgave colorless oil, bp 175° (2 mmHg)

Sources & evidence

ORD record
ord-8445572479b845f18da771af8eff1ae7
Source dataset
uspto-grants-1978_06
Patent number
US04097483

Reaction notes

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