Ammonia → Methyl 6-bromopyridine-2-carboxylate
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N.[CH3:17]O>>[CH3:17][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)=[O:10]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
6-Bromopyridine-2-carboxylic acid (6.000 g) was heated in refluxing methanol (180 mL) containing conc. sulphuric acid (2 mL) for 4 hrs. The reaction mixture was then cooled to ˜0° C. and conc. ammonia (4.8 mL) was added. The resulting solution was evaporated to give a white residue. This white solid was partitioned between brine and dichloromethane (100/100 mL). After thorough shaking the organic layer was dried (magnesium sulphate) and evaporated to give a white solid.
Workup
- customThe resulting solution was evaporated
- customto give a white residue
- customThis white solid was partitioned between brine and dichloromethane (100/100 mL)
- dry with materialwas dried (magnesium sulphate)
- customevaporated
- customto give a white solid
Sources & evidence
- ORD record
- ord-1d2be00d738e44ccba8a9553e59a0153
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232821B2
Reaction notes
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