Water → (+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde

HRID 346989ノート

反応式

HRID 346989 の反応式
I[CH3:2].Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:36])([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)[C:22]4[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=4)[CH:19]=3)[NH:14][C:13](=[O:37])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1.O>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].[OH-].[Na+].C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:36])([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)[C:22]4[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=4)[CH:19]=3)[N:14]([CH3:2])[C:13](=[O:37])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1

参加物

7

反応物 3

HCID 962WaterHCID 6328Methyl iodideHCID 21082104(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde monohydrochloride

生成物 1

HCID 10299684(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde収率 32%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

BTEAC (0.00395 mol), then iodomethane (0.00474 mol) were added to a solution of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5yl)methyl]benzaldehyde monohydrochloride (described in Example B1) (0.00395 mol) in NaOH (1N) and THF (20 ml). The mixture was stirred at room temperature for 18 hours, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.87 g) was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 0.61 g (32%) of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde, mp. 208° C.

後処理

  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 (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue (0.87 g) was crystallized from diethyl ether
  10. filtrationThe precipitate was filtered off
  11. customdried

出典と根拠

ORDレコード
ord-df411440408a42dba154584c8840f70d
出典データセット
uspto-grants-2007_02
特許番号
US07173040B2

反応ノート

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