Ammonium formate → Methyl 5-amino-6-methylnicotinate

HRID 1521342Notes

Reaction equation

HRID 1521342 reaction equation
Cl[C:2]1[N:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:13][C:9]1[C:10]([CH3:12])=[N:11][CH:2]=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86672545Methyl 2-chloro-6-methyl-5-nitronicotinate

Product 1

HCID 58662456Methyl 5-amino-6-methylnicotinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-chloro-6-methyl-5-nitronicotinate (step 1) (6.9 g, 29.9 mmol) was added to a suspension of ammonium formate (18.87 g, 299 mmol) and 10% Pd (Carbon) (0.522 g, 0.491 mmol) in MeOH (330 ml) and the mixture was heated at reflux for 3 hrs. After cooling to RT, the mixture was filtered through Celite® (filter material) and washed through with MeOH. The solvent was removed in vacuo and the crude product was triturated with EtOAc to give an orange solid. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hrs
  3. filtrationthe mixture was filtered through Celite® (filter material)
  4. washwashed through with MeOH
  5. customThe solvent was removed in vacuo
  6. customthe crude product was triturated with EtOAc
  7. customto give an orange solid
  8. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-7f938c882d7e43b0b1924b2432e31fa5
Source dataset
uspto-grants-2015_07
Patent number
US09073921B2

Reaction notes

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