3-Chloropropionyl chloride → HCID 21258081, compound

HRID 635269Notes

Reaction equation

HRID 635269 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[N:3]1.[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:11][CH2:12][CH2:13][C:14]([C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:2]([CH3:1])[N:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13549259HCID 13549259, compound

Product 1

HCID 21258081HCID 21258081, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4,5,6,7-Tetrahydro-1-methyl-1H-indazole (10 g) and 3-chloropropionyl chloride (26 g) were dissolved in dichloroethane (100 ml) and aluminum chloride (28 g) was gradually added under an ice bath while stirring the mixture The reaction mixture was stirred for 17 hours at room temperature and poured into ice water. The reaction mixture was stirred for 2 hours at room temperature and extracted twice with chloroform. The chloroform layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over magnesium sulfate. The magnesium sulfate was filtered off and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (silica gel 100 g) and 3-(3-chloropropionyl)-4,5,6,7-tetrahydro-1-methyl-1H-indazole (10 g) was obtained from an eluate of hexane:ethyl acetate=20:1.

Workup

  1. stirringwas stirred for 17 hours at room temperature
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. extractionextracted twice with chloroform
  4. washThe chloroform layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtered off
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf5f50fc4f0d43cda0a9b82f1411e656
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

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