Ammonium formate → HCID 15239995, compound

HRID 1653647Notes

Reaction equation

HRID 1653647 reaction equation
[N:1]([C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([O:14]CC2C=CC=CC=2)=[CH:6][CH:5]=1)=[N+]=[N-].C([O-])=O.[NH4+]>[C].[Pd].CO>[NH2:1][C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([OH:14])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15239994HCID 15239994, compound

Product 1

HCID 15239995HCID 15239995, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a methanol (80 ml) suspension of 7 g (24.6 mmol) of methyl 6-azido-3-benzyloxypicolinate in a 200 ml round bottomed flask, 1 g of palladium carbon (10%) was added under a nitrogen gas stream, and 7.8 g (123 mmol) of ammonium formate was further added thereto. The mixture was stirred at room temperature for 12 hours. The catalyst was filtered off, and the filtrate was concentrated and dissolved in chloroform. The solvent was washed with water, dried and concentrated. Crystals thereby formed were collected by filtration and washed with diisopropyl ether to obtain 3.57 g (yield: 86.3%) of methyl 6-amino-3-hydroxypicolinate.

Workup

  1. additionwas further added
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutiondissolved in chloroform
  5. washThe solvent was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customCrystals thereby formed
  9. filtrationwere collected by filtration
  10. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-a37e8c3a594d4c319fe61b5569ba3e84
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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