Methanol → Methyl 5-methylisoxazole-3-carboxylate
Reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.S(=O)(=O)(O)O.[CH3:15]O>>[CH3:15][O:8][C:7]([C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1)=[O:9]Participants
4
Procedure
2,5-Hexanedione, 9 is the starting material for the process. 2,5-Hexanedione 9 is nitrated and oxidized with nitric acid to form 5-methyl-3-isoxazolecarboxlic acid 8, (isoxazole acid). Isoxazole acid 8 is esterified by treating it with methyl alcohol and sulfuric acid to give 5-methyl-3-isoxazolecarboxylic acid methyl ester, isoxazole ester 7. Isoxazole ester 7 is reacted with Benzylhydrazine 5 which itself is prepared from the reaction of benzaldehyde 6 with hydrazine and then reduced with hydrogen to form Benzylhydrazine 5.
Sources & evidence
- ORD record
- ord-04746eef1fe940f7bd2ed33bbab526c8
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518254B1
Reaction notes
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