Tetrahydrofuran → HCID 21082080, compound

HRID 347001Notes

Reaction equation

HRID 347001 reaction equation
Cl[C:2]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)([C:22]1[N:26]([CH3:27])[CH:25]=[N:24][N: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.C1COCC1.[NH3:40].CC(O)C>O>[NH2:40][C:2]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)([C:22]1[N:26]([CH3:27])[CH:25]=[N:24][N: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

5

Reactant 3

HCID 8028TetrahydrofuranHCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 210820836-[chloro(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

Product 1

HCID 21082080HCID 21082080, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-[chloro(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (0.0045 mol) was added at 5° C. to THF (25 ml) under N2 flow. NH3/2-propanol saturated (25 ml) was added dropwise. The mixture was kept for 1 hour, poured out into water and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue (2.6 g) was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH; 50/50/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (1.6 g, 73%) was crystallized from CH3CN/DIPE. The precipitate was filtered off and dried. The residue (1.3 g, 59%) was purified by column chromatography over kromasil 10 μm (eluent: CH3OH/H2O; 60/40). The pure fractions were collected and the solvent was evaporated. The residue (1.4 g, 63%) was crystallized from CH3CN/DIPE. The precipitate was filtered off and dried, yielding 1.26 g (57%) of 6-[amino(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone, mp. 210° C.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (2.6 g) was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH; 50/50/1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue (1.6 g, 73%) was crystallized from CH3CN/DIPE
  10. filtrationThe precipitate was filtered off
  11. customdried
  12. customThe residue (1.3 g, 59%) was purified by column chromatography over kromasil 10 μm (eluent: CH3OH/H2O; 60/40)
  13. customThe pure fractions were collected
  14. customthe solvent was evaporated
  15. customThe residue (1.4 g, 63%) was crystallized from CH3CN/DIPE
  16. filtrationThe precipitate was filtered off
  17. customdried

Sources & evidence

ORD record
ord-b452c5a95abc4188aac2dbe12bae2597
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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