2-Propanol, reaction products with ammonia, distn. residues → HCID 10182046, compound

HRID 1830819Notes

Reaction equation

HRID 1830819 reaction equation
Cl[C:2]([C:28]1[CH:32]=[CH:31][O:30][CH:29]=1)([C:22]1[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1.CC(O)C.[NH3:37]>C1COCC1>[NH2:37][C:2]([C:28]1[CH:32]=[CH:31][O:30][CH:29]=1)([C:22]1[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1

Participants

4

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 22048479HCID 22048479, compound

Product 1

HCID 10182046HCID 10182046, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 6-[chloro-3-furanyl(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (obtained in stage b) (0.0045 mol) in THF (30 ml) was cooled to 5° C. 2-Propanol-NH3 saturated (30 ml) was added dropwise quickly. The mixture was stirred at room temperature for 1 hour. The solvent was evaporated till dryness. The residue was taken up in DCM and water and the mixture was decanted. The organic layer was dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (2.2 g) was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 85/13/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN and DIPE. The precipitate was filtered off and dried, yielding 0.55 g (27.5%) of (±)-6-[amino-3-furanyl(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone, melting point 197° C.

Workup

  1. customThe solvent was evaporated till dryness
  2. customwater and the mixture was decanted
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (2.2 g) was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 85/13/1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from CH3CN and DIPE
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-09595f6d55304df99094ea6832488ef9
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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