Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([F:17])[C:8]([F:16])=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[CH:11]=[CH:10]2)=[O:4].O.[H][H]>C(O)(=O)C.[Pt]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([F:17])[C:8]([F:16])=[C:9]2[C:14]=1[NH:13][CH:12]([CH3:15])[CH2:11][CH2:10]2)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 8.0 g (33.7 mmol) of 5,6-difluoro-2-methylquinoline-8-carboxylic acid methyl ester (Example 33) in 100 mL of glacial acetic acid is treated with 2.15 g of platinum on carbon (0.8 g of active catalyst+62.8% water) and then shaken in a hydrogen atmosphere at temperatures of 24° C. to 29° C. and pressures of 23.9 to 46.6 psi for 3 hours. The catalyst is removed by filtration and the solvent is removed in vacuo at 50° C. The residue is triturated with water (50 mL) and extracted with dichloromethane (2×200 mL). The combined organic layers are stirred with 5% sodium bicarbonate solution, washed with water, dried (MgSO4), filtered and evaporated in vacuo. The residue is chromatographed over flash grade silica gel (230–400 mesh) eluting with dichloromethane to give 5.6 g of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3): 7.66 (bs, 1H), 7.49 (m, 1H), 3.82 (s, 3H), 3.46 (m, 1H), 2.88 (m, 1H), 2.67 (m, 1H), 1.97 (m, 1H), 1.27 (d, 3H).
Workup
- customThe catalyst is removed by filtration
- customthe solvent is removed in vacuo at 50° C
- customThe residue is triturated with water (50 mL)
- extractionextracted with dichloromethane (2×200 mL)
- washwashed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
- customThe residue is chromatographed over flash grade silica gel (230–400 mesh)
- washeluting with dichloromethane
Sources & evidence
- ORD record
- ord-cf7993e3573e421a894de7cb83cffe3e
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094780B1
Linked notes
Loading…