Potassium Carbonate → HCID 22136469, compound

HRID 1827267Notes

Reaction equation

HRID 1827267 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]([C:18]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)([C:20]4[N:24]([CH3:25])[C:23](S)=[N:22][N:21]=4)[OH:19])[CH:16]=3)[N:11]=[C:10]([CH3:34])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[N+]([O-])(O)=O.O>[OH2:19].[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:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][N:21]=4)[OH:19])[CH:16]=3)[N:11]=[C:10]([CH3:34])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178422657HCID 178422657, compound

Product 1

HCID 22136469HCID 22136469, compoundYield 101.3%

Reagents, catalysts & solvents 3

HCID 944Nitric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(5-mercapto-4-methyl-4H-1,2,4-triazol-3-yl)-2-methyl-6-quinolinemethanol (0.0020 mol), obtained in Example B14a, in THF (5 ml) was added dropwise at 5° C. to a mixture of sodium nitrite (0.0020 mol) in nitric acid (2 ml) and water (2 ml). The mixture was stirred at 5° C. for 5 minutes, poured out into potassium carbonate 10% and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over kromasil 10 μm (eluent: CH2Cl2/CH3OH; 90/10). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.5 g (53%) of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-methyl-α-(4-methyl-4H-1,2,4-triazol-3-yl)-6-quinolinemethanol monohydrate, mp. 150° C.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over kromasil 10 μm (eluent: CH2Cl2/CH3OH; 90/10)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-5adff23433ae47e9925cd2f6ffba32c2
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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