Water → 4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone

HRID 346993Notes

Reaction equation

HRID 346993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][N:20]=4)[CH:16]=3)[N:11]([CH3:32])[C:10](=[O:33])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CC([OH:38])(C)C.[K].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=4)([OH:38])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][N:20]=4)[CH:16]=3)[N:11]([CH3:32])[C:10](=[O:33])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 5462222PotassiumHCID 98910924-(3-chlorophenyl)-6-[(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone

Product 1

HCID 210820404-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinoneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Air was bubbled in a mixture of 4-(3-chlorophenyl)-6-[(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone (see Example B7) (0.0018 mol) in N,N-dimethylformamide (8 ml) at 5° C. for 30 minutes. 2-methyl-2-propanol, potassium salt (0.0036 mol) was added portionwise. The mixture was stirred at room temperature for 1 hour, poured out into water, filtered and washed several times with water. The precipitate was taken up in CH2Cl2. The organic layer was separated dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.75 g, 85%) was crystallized from 2 propanone/DIPE. The precipitate was filtered off and dried, yielding 0.68 g (77%) of 4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone, mp. 182° C.

Workup

  1. filtrationfiltered
  2. washwashed several times with water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness
  7. customThe residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/0.1; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue (0.75 g, 85%) was crystallized from 2 propanone/DIPE
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-014d07dba33e471aa8e47a64453679b7
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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