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

HRID 2288472Notes

Reaction equation

HRID 2288472 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-nitro-nicotinate (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. Yield: 0.75 g (81% of theory) of greenish-yellow solid, Rf value: 0.31 (silica gel;ethyl acetate/petroleum ether=1:4) C7H7ClN2O2 (186.60) YEF- Mass spectrum: M+ =186 and 188 (chlorine isotopes).

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-439649ead08d4f45962c3aa89bbf9ad1
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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