Nitrogen → 6-[2-chloro-1-(4-chlorophenyl)-1-(4-methyl-4H-1,2,4-triazol-3-yl)ethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

HRID 347012Notes

Reaction equation

HRID 347012 reaction equation
N#N.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:20]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:21]4[N:25]([CH3:26])[CH:24]=[N:23][N:22]=4)[CH:18]=3)[N:13]([CH3:34])[C:12](=[O:35])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[CH2:36](Cl)[Cl:37].[K]>COCCOC.O.CC(O)C>[Cl:37][CH2:36][C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:34])[C:12](=[O:35])[CH:11]=[C:10]2[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=1)([C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:21]1[N:25]([CH3:26])[CH:24]=[N:23][N:22]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 6344DichloromethaneHCID 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 210820746-[2-chloro-1-(4-chlorophenyl)-1-(4-methyl-4H-1,2,4-triazol-3-yl)ethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinoneYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N2 was bubbled at room temperature to a solution of 4-(3-chlorophenyl)-6-[(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone (0.00105 mol), obtained in Example B7, in DME (8.5 ml) for 30 minutes. DCM (2 ml) was added. Then 2-methyl, 2-propanol, potassium salt (0.0021 mol) was added portionwise. The mixture was stirred for 1 hour, poured out into water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue (0.55 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100 to 95/5; 10 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.35 g, 64%) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.28 g (51%) of 6-[2-chloro-1-(4-chlorophenyl)-1-(4-methyl-4H-1,2,4-triazol-3-yl)ethyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone, mp. 260° C.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (0.55 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100 to 95/5; 10 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue (0.35 g, 64%) was crystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-da640ebed7f649e28aef06620a2709a4
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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