Hydrochloric Acid → Methyl 5-amino-6-chloropyridine-3-carboxylate

HRID 2227668Notes

Reaction equation

HRID 2227668 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.O.Cl>C(O)C.[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

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 346961Methyl 6-chloro-5-nitronicotinate

Product 1

HCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of 1.08 g (5.00 mmol) of methyl 6-chloro-5-nitronicotinate (see A. H. Berrie, G. T. Newbold, F. S. Spring in J. Chem. Soc., 2590, 1951) in 25 ml of absolute ethanol was mixed successively with 0.53 ml (29 mmol) of water, 3.2 g (57 mmol) of iron powder and 0.030 ml of concentrated hydrochloric acid and heated to boiling for one hour. Then equal quantities of water, iron powder and hydrochloric acid were added and the mixture was heated to boiling for 30 minutes. The precipitate formed on cooling was filtered off and washed with ethanol and the solvent was distilled off in vacuo.

Workup

  1. temperatureheated
  2. temperaturethe mixture was heated
  3. waitto boiling for 30 minutes
  4. customThe precipitate formed
  5. temperatureon cooling
  6. filtrationwas filtered off
  7. washwashed with ethanol
  8. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-d81436a0b91445e8813fd10a4276132e
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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