Pyridine → 5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide

HRID 926855Notes

Reaction equation

HRID 926855 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].N1C=CC=CC=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N+:31]([O-:33])=[O:32])=[C:26]([CH:30]=1)[C:27](Cl)=[O:28]>ClCCl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N+:31]([O-:33])=[O:32])=[C:26]([CH:30]=1)[C:27]([NH:14][C:11]1[CH:12]=[CH:13][N:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[N:10]=1)=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27236855-Chloro-2-nitrobenzoyl chlorideHCID 28301245HCID 28301245, compound

Product 1

HCID 665874615-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of 1-(3,4-dimethylphenyl)-1H-pyrazol-3-amine (408 mg, 2.18 mmol, 1.00 equiv) in dichloromethane (10 mL), pyridine (518 mg, 6.56 mmol, 3.00 equiv), and 5-chloro-2-nitrobenzoyl chloride (575 mg, 2.61 mmol, 1.00 equiv). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The solution was adjusted to pH 7 with hydrochloric acid (1 mol/L). The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in 600 mg (59%) of 5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide as a yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
  4. dry with materialthe organic layers combined dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 600 mg (59%) of 5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide as a yellow solid

Sources & evidence

ORD record
ord-ca13dc2758274442bf63d8e6d8af3783
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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