2,4-Dichlorobenzyl chloride → HCID 16202559, compound

HRID 2108941Notes

Reaction equation

HRID 2108941 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17]Cl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(Cl)Cl>[CH3:13][O:12][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:17][C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=2[Cl:14])[N:2]=1)=[O:11]

Participants

6

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 657476methyl 1H-indazole-3-carboxylate

Product 1

HCID 16202559HCID 16202559, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Next, a mixture of methyl indazole-3-carboxylate (2.05 g, 11.4 mmol), 2,4-dichlorobenzyl chloride (3.35 mL, 12.54 mml), and K2CO3 (7.0 g, 50 mmol) in acetone (22 mL) was refluxed overnight at a temperature of 70° C. The reaction mixture was cooled to room temperature, filtered, and the residue was washed with acetone. The combined filtrate was concentrated under vacuum (rotovapor). The solid thus obtained was dissolved in CH2Cl2 and filtered to remove any undissolved solid. The solution was then concentrated, diluted with hexane and left in the refrigerator overnight. The precipitated solid was then filtered, washed with a mixture of hexane/ethyl acetate (9:1) to yield the pure product as a white solid. Yield=3.5 g (89%); m.p.=144°-146° C.; 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=8.8 Hz, 1H), 7.39-7.47 (m, 4H), 7.12 (d, J=8.8 Hz, 1H), 6.71 (d, J=8.8 Hz, 1H), 5.81 (s, 2H), 4.11 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washthe residue was washed with acetone
  4. concentrationThe combined filtrate was concentrated under vacuum (rotovapor)
  5. customThe solid thus obtained
  6. filtrationfiltered
  7. customto remove any undissolved solid
  8. concentrationThe solution was then concentrated
  9. additiondiluted with hexane
  10. filtrationThe precipitated solid was then filtered
  11. washwashed with a mixture of hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-d18e2a33a871474aa1c1bc97d4c3793a
Source dataset
uspto-grants-2009_04
Patent number
US07514463B2

Reaction notes

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