Hydrochloric Acid → 5-Fluoro-2,3-pyridinediamine

HRID 550374Notes

Reaction equation

HRID 550374 reaction equation
Cl.[N:2]([C:5]1[C:6]([NH2:12])=[N:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[N+]=[N-].C(=O)([O-])[O-]>O1CCCC1>[F:11][C:9]1[CH:10]=[C:5]([NH2:2])[C:6]([NH2:12])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 222932423-Azido-5-fluoropyridin-2-amine

Product 1

HCID 222931555-Fluoro-2,3-pyridinediamineYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The HCl salt of 3-azido-5-fluoropyridin-2-amine (1.90 g, 10.0 mmol) was dissolved in tetrahydrofuran (100 mL) and treated with MP-Carbonate (Argonaut, 11.5 g). After 1 h, the mixture was filtered, rinsed with more tetrahydrofuran, and concentrated. This residue was dissolved in ethanol (50 mL), purged with argon, and 10% palladium on carbon was added (0.15 g). Hydrogen was introduced (1 atm) and the reaction stirred until complete. The catalyst was filtered and the solvent evaporated from the filtrate to give the title compound (1.18 g). MS: m/z=128.0 (M+1)

Workup

  1. filtrationthe mixture was filtered
  2. washrinsed with more tetrahydrofuran
  3. concentrationconcentrated
  4. dissolutionThis residue was dissolved in ethanol (50 mL)
  5. custompurged with argon, and 10% palladium on carbon
  6. additionwas added (0.15 g)
  7. additionHydrogen was introduced (1 atm)
  8. filtrationThe catalyst was filtered
  9. customthe solvent evaporated from the filtrate

Sources & evidence

ORD record
ord-8657b51bf3804132a075044911f07774
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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