Hydrazine hydrate (1:1) → 4-(4-methoxyphenyl)-3-methylisoxazolo[3,4-d]pyridazin-7(6H)-one

HRID 1186883Notes

Reaction equation

HRID 1186883 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:9]([CH3:21])[O:8][N:7]=1)=O)C.O.[NH2:23][NH2:24]>C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[C:10]3[C:6](=[N:7][O:8][C:9]=3[CH3:21])[C:4](=[O:3])[NH:23][N:24]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596520274-(4-Methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester

Product 1

HCID 441218194-(4-methoxyphenyl)-3-methylisoxazolo[3,4-d]pyridazin-7(6H)-oneYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.47 g of 4-(4-methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester (8.54 mmol) and 0.598 mL of hydrazine monohydrate (12.0 mmol) in 18.4 mL ethanol was stirred at room temperature for 19 hours. The heterogeneous reaction was cooled in an ice bath then filtered off the white solid, washing with cold ethanol then diethyl ether. Dried on under high vacuum to give 2.06 g (92%) of 4-(4-methoxyphenyl)-3-methyl-6 h-isoxazolo[3,4-d]pyridazin-7-one.

Workup

  1. customThe heterogeneous reaction
  2. temperaturewas cooled in an ice bath
  3. filtrationthen filtered off the white solid
  4. washwashing with cold ethanol
  5. customDried on under high vacuum

Sources & evidence

ORD record
ord-c0a8bac38d1949e2b854a35c60a1c682
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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