Dichloromethane → 1-Cyclopropyl-1H-pyrazole-4-carboxaldehyde

HRID 220484Notes

Reaction equation

HRID 220484 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH:14]1(Br)[CH2:16][CH2:15]1.C(Cl)Cl>CN(C)C=O.O>[CH:14]1([N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 78037BromocyclopropaneHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 574169141-Cyclopropyl-1H-pyrazole-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Dissolve 1H-pyrazole-4-carboxaldehyde in N,N-dimethylformamide (1.9 mL). Add potassium carbonate (0.539 g, 3.90 mmol) and cyclopropylbromide (0.346 g, 2.86 mmol). Heat in a pressure tube to 130° C. for 18 hr. Cool to ambient temperature and add DCM and water. Separate layers and extract water layer 3 times with DCM. Wash combined DCM layers with brine, dry (magnesium sulfate), filter, and concentrated to give the free base of the title preparation. GC-MS: m/z=136 [M+].

Workup

  1. temperatureCool to ambient temperature
  2. extractionSeparate layers and extract water layer 3 times with DCM
  3. washWash
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrated
  7. customto give the free base of the title
  8. custompreparation

Sources & evidence

ORD record
ord-0795e3ea283f4c93b15e1240568b2a55
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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