Methanol → methyl 3-nitro-1H-pyrazole-5-carboxylate
Reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)([O-:3])=[O:2].[CH3:12]O>>[CH3:12][O:10][C:9]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=1)=[O:11]Participants
3
Procedure
A solution of 5-nitro-1H-pyrazole-3-carboxylic acid (17, Aldrich, cat. no. 41,483-2) in MeOH was prepared. While stirring, HCl was bubbled through the solution for 2 min. The reaction mixture was refluxed for a time sufficient for complete esterification and allowed to cool to rt. The solvent was removed by rotary evaporation. The crude material was basified by addition of saturated aqueous NaHCO3 and extracting with EtOAc. The combined organic extracts were dried over MgSO4 and filtered. The filtrate was rotary evaporated and dried under vacuum to yield 18.
Workup
- customHCl was bubbled through the solution for 2 min
- temperatureThe reaction mixture was refluxed for a time sufficient for complete esterification
- customThe solvent was removed by rotary evaporation
- additionThe crude material was basified by addition of saturated aqueous NaHCO3
- extractionextracting with EtOAc
- dry with materialThe combined organic extracts were dried over MgSO4
- filtrationfiltered
- customThe filtrate was rotary evaporated
- customdried under vacuum
Sources & evidence
- ORD record
- ord-80fb3a64f09446989947c9b538d72cf2
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432379B2
Reaction notes
Loading…