Ammonium formate → Methyl 5-amino-6-methylnicotinate

HRID 335312Notes

Reaction equation

HRID 335312 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>[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

4

Reactant 2

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

Product 1

HCID 58662456Methyl 5-amino-6-methylnicotinate

Reagents, catalysts & solvents 1

HCID 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-46e6da5b281d4b7aaa696135f0584238
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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