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

HRID 2042620Notes

Reaction equation

HRID 2042620 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-6h-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-2b8552698881414cbcdd8af6867b9095
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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