HCID 67387799, compound → 2-Amino-5-fluoropyridin-3-ol

HRID 908418Notes

Reaction equation

HRID 908418 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O-:11])[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.[Na+]>C(O)C.[Pt](=O)=O>[NH2:8][C:5]1[C:4]([OH:11])=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 67387799HCID 67387799, compound

Product 1

HCID 214366912-Amino-5-fluoropyridin-3-olYield 11.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of sodium 5-fluoro-2-nitro-pyridin-3-olate (7.3 g) and platinum(IV) oxide (0.092 g) in ethanol (20 ml) at 25° C., was hydrogenated under 3.5 atm at 25° C. for 30 minutes. The resulting black suspension was filtered through a pad of Dicalite Speed Plus (Acros Chemicals) and hydrogen chloride 4M in dioxane (4.26 ml) was added to the filtrate. The suspension was filtered and concentrated to a black oil, which was triturated in diethyl ether, the precipitate was collected by filtration and dried to afford the crude 2-amino-5-fluoro-pyridin-3-ol (0.607 g) hydrochloride salt. NMR Spectrum: (DMSOd6) 7.23 (dd, 1H), 7.65 (dd, 1H), 7.82 (bs, 2H), 12.23 (bs, 1H).

Workup

  1. filtrationThe resulting black suspension was filtered through a pad of Dicalite Speed Plus (Acros Chemicals) and hydrogen chloride 4M in dioxane (4.26 ml)
  2. additionwas added to the filtrate
  3. filtrationThe suspension was filtered
  4. concentrationconcentrated to a black oil, which
  5. customwas triturated in diethyl ether
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-11bb1ac8f4b44b38b0faeb6426146062
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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