Isopropyl iodide → 2-i-propyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

HRID 1111133Notes

Reaction equation

HRID 1111133 reaction equation
[Cl:1][C:2]1[C:3](=[O:25])[NH:4][N:5]=[C:6]([N+:22]([O-:24])=[O:23])[C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH3:21])[CH:11]=1.[CH:26](I)([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH:26]([N:4]1[C:3](=[O:25])[C:2]([Cl:1])=[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH3:21])[CH:11]=2)[C:6]([N+:22]([O-:24])=[O:23])=[N:5]1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 150790474-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

Product 1

HCID 150790502-i-propyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture comprising 500 mg of 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone (Compound No. 22) prepared in Example 2, 691 mg of isopropyl iodide, 562 mg of anhydrous potassium carbonate and 25 ml of methyl ethyl ketone, was refluxed under stirring for 1.5 hours. The solvent was distilled off under reduced pressure, and water was added to the residue thereby obtained. The mixture was extracted with diethyl ether. The extract was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. Then, the solvent was distilled off. The residual oily substance thereby obtained was crystallized from a solvent mixture of diethyl ether-n-hexane, to obtain 435 mg of the above identified compound having a melting point of from 82.5° to 84° C. as yellow crystals.

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customthereby obtained
  5. extractionThe mixture was extracted with diethyl ether
  6. washThe extract was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customThe residual oily substance thereby obtained
  10. customwas crystallized from a solvent mixture of diethyl ether-n-hexane
  11. customto obtain 435 mg of the
  12. customof from 82.5° to 84° C.

Sources & evidence

ORD record
ord-fbb1d3b35b924e828dbd14fdac21a508
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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