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

HRID 271891Notes

Reaction equation

HRID 271891 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 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-00caae43ca374be58b46c1b6e458e84a
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Reaction notes

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