Chlorosuccinimide → Ethyl 6-amino-5-chloronicotinate

HRID 1789880Notes

Reaction equation

HRID 1789880 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[N:15][CH:14]=1)[CH3:10]>C(#N)C>[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[C:17]([Cl:1])[C:16]([NH2:19])=[N:15][CH:14]=1)[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 235927Ethyl 6-Aminonicotinate

Product 1

HCID 53757847Ethyl 6-amino-5-chloronicotinateYield 79.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (21.7 g, 0.162 mol) was added to a suspension of 6-amino-nicotinic acid ethyl ester (18.0 g, 0.108 mol) in acetonitrile (270 ml) and the mixture was refluxed for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with water and dried. Flash chromatography (2.5% MeOH in CH2Cl2) gave pure 6-amino-5-chloro-nicotinic acid ethyl ester (17.23 g, 79%).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2ced570083014538a0270a15b33675f2
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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