Methyl 6-chloro-5-nitronicotinate → Methyl 5-amino-6-chloropyridine-3-carboxylate

HRID 453276Notes

Reaction equation

HRID 453276 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

HCID 346961Methyl 6-chloro-5-nitronicotinate

Product 1

HCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

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

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac6e5532c22546a68a8f5d2ab19e2282
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

Loading…