Ammonia → Furo[3,2-c]pyridin-4-amine

HRID 1910659Notes

Reaction equation

HRID 1910659 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH3:11]>[Cu]Cl>[O:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:11])[C:7]=2[CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27797464-Chlorofuro[3,2-c]pyridine

Product 1

HCID 22665882Furo[3,2-c]pyridin-4-amineYield 95%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
150 °C

Procedure

65.3 g (425 mmol) 4-chlorofuro[3,2-c]pyridine [CAS Reg.-No. 31270-80-1] were suspended in 600 ml aqueous ammonia solution (35%) in an autoclave. After addition of 2 g copper(I)-chloride, the reaction mixture was stirred for 20 h at 150° C. After cooling to rt, the mixture was extracted with dichloromethane (3×400 ml). The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 46.6 g (82% of th.) of crude title compound (content >95% by GC) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture was extracted with dichloromethane (3×400 ml)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-872275196f884867be503781014fef37
Source dataset
uspto-grants-2013_12
Patent number
US08604028B2

Reaction notes

Loading…