Methyl 6-chloro-5-nitronicotinate → Methyl 5-amino-6-chloropyridine-3-carboxylate
Reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1>CO.[Fe]>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
A suspension of methyl 6-chloro-5-nitronicotinate (1 eq), iron powder (5.2 eq), and NH4Cl3 (5.3 eq) in MeOH was heated at 75° C. for 2 h. The mixture was passed through a pad of celite while hot and concentrated in vacuo to give methyl 5-amino-6-chloronicotinate (56% yield).
Workup
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6cd4ac09723e472986346268bd16589c
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343997B2
Reaction notes
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