Water → HCID 10186034, compound

HRID 347002Notes

Reaction equation

HRID 347002 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:35])([C:29]2[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]3[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[CH:5][CH:4]=1.[CH3:36][CH2:37][O-:38].[Na+].CCO.O>C(O)C>[Cl:28][C:24]1[CH:23]=[C:22]([C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][O:38][CH2:37][CH3:36])=[CH:4][CH:5]=4)([OH:35])[C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[CH:11]=3)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21082106(+/-)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinoneHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 10186034HCID 10186034, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (0.0002 mol), obtained in Example B14, and EtONa/EtOH (0.0005 mol) in ethanol (1 ml) was stirred at room temperature for 18 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.1 g) was purified by column chromatography over kromasil 10 μm (eluent: CH2Cl2/CH3OH; 90/10). The pure fractions were collected and the solvent was evaporated, yielding 0.034 g (33%) of 4-(3-chlorophenyl)-6-[[4-(ethoxymethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, as a white foam, MS (ESI) m/z:514, 516 (MH+).

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 (0.1 g) 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

Sources & evidence

ORD record
ord-4eb8cc3280584d37b17b1386e9d0f72d
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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