Pyridine → HCID 58551882, compound

HRID 453277Notes

Reaction equation

HRID 453277 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[C:9]([Cl:18])=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14].[N+:19]([C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])([O-:21])=[O:20]>C(Cl)Cl>[Cl:18][C:9]1[C:8]([NH:7][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[N+:19]([O-:21])=[O:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

Product 1

HCID 58551882HCID 58551882, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.1 eq) was added to a solution of methyl 5-amino-6-chloronicotinate (1 eq) and 2-nitrobenzoyl chloride (1.2 eq) in CH2Cl2. The mixture was stirred at room temperature for 10 h and concentrated in vacuo. H2O was added and the resultant solid was collected by filtration, rinsed with CH2Cl2 and dried to give methyl 6-chloro-5-(2-nitrobenzamido)nicotinate (73% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additionH2O was added
  3. filtrationthe resultant solid was collected by filtration
  4. washrinsed with CH2Cl2
  5. customdried

Sources & evidence

ORD record
ord-9615e9f71e2543498218ac1c298d1a88
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

Loading…