Acetic Acid → 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-amino-3(2H)pyridazinone

HRID 1111131Notes

Reaction equation

HRID 1111131 reaction equation
[Cl:1][C:2]1[C:3](=[O:25])[NH:4][N:5]=[C:6]([N+:22]([O-])=O)[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.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)(=O)C>C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[C:3](=[O:25])[NH:4][N:5]=[C:6]([NH2:22])[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

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24489Sodium DithioniteHCID 150790474-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

Product 1

HCID 150790484-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-amino-3(2H)pyridazinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

1.00 g of 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone (Compound No. 22) prepared in Example 2, was dissolved in a solvent mixture of 20 ml of ethanol and 20 ml of a 10% sodium carbonate aqueous solution, 3.30 g of sodium hydrosulfite was gradually added thereto at room temperature under stirring. The mixture was stirred at room temperature for 1 hour, and was neutralized with glacial acetic acid. Then, ethanol was distilled off under reduced pressure, and water was added to the residue thereby obtained. The mixture was extracted with chloroform. The extract was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. Then, the solvent was distilled off to obtain light yellow crystals This product was crystallized from a solvent mixture of methanol-diethyl ether, to obtain 634 mg of the above identified compound having a melting point of from 187.5° to 189.5° C. as colorless crystals

Workup

  1. additionwas gradually added
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. distillationThen, ethanol was distilled off under reduced pressure, and water
  4. additionwas added to the residue
  5. customthereby obtained
  6. extractionThe mixture was extracted with chloroform
  7. washThe extract was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over sodium sulfate
  9. distillationThen, the solvent was distilled off
  10. customto obtain light yellow crystals This product
  11. customwas crystallized from a solvent mixture of methanol-diethyl ether
  12. customto obtain 634 mg of the
  13. customof from 187.5° to 189.5° C.

Sources & evidence

ORD record
ord-96fa27fc2a8249219c521c53f1c9bc2b
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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