Ammonium formate → 4-Methoxyquinolin-8-amine

HRID 513422Notes

Reaction equation

HRID 513422 reaction equation
Cl[C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6]([O:13][CH3:14])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].C(O)(=O)C>[CH3:14][O:13][C:6]1[C:5]2[C:10](=[C:11]([NH2:12])[CH:2]=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 681832377-Chloro-4-methoxyquinolin-8-amine2×

Product 1

HCID 122706624-Methoxyquinolin-8-amineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% palladium on carbon (125 mg, 1.1 mmol) was added to a solution of 7-chloro-4-methoxy-quinolin-8-ylamine (Intermediate 70) (246 mg, 1.1 mmol), and ammonium formate (365 mg, 5.8 mmol) in 50% acetic acid (5 ml) and the reaction was heated under reflux for 30 min. After cooling the solvent was removed in vacuo. The residue was dissolved in EtOAc (100 ml) and washed with sat sodium bicarbonate solution, dried (MgSO4) and concentrated in vacuo to give the title compound (124 mg, 65%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling the solvent
  4. customwas removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (100 ml)
  6. washwashed
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e30d813dc744a419a1ca62d17e8668a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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