Water → 6-chloropyridazine-3-carboxylic Acid
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[OH2:9].[OH:10]S(O)(=O)=O>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 3-chloro-6-methylpyridazine (12.8 g, 100 mol) in concentrated H2SO4 (100 mL) was added powered K2Cr2O7 (35.3 g, 120 mmol) slowly at 50° C. The reaction mixture was stirred at 50° C. for 4 h, and poured into the iced water carefully. The mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed under vacuum to afford the 6-chloropyridazine-3-carboxylic acid (9.25 g, 59%), which was used directly in the next step. 1H NMR (DMSO-d6, 400 MHz): δ8.21 (d, J=4.8 Hz, 1H), 8.06 (d, J=4.8 Hz, 1H).
Workup
- extractionThe mixture was extracted with EtOAc
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-cdadc9b154d6479a8ba2307c4d668e26
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569292B2
Reaction notes
Loading…