Nitric Acid → 4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-alpha-(4-methyl-4H-1,2,4-triazol-3-yl)-6-quinolinemethanol

HRID 346980ノート

反応式

HRID 346980 の反応式
N([O-])=O.[Na+].[N+]([O-])(O)=O.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([C:35]4[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=4)([C:28]4[N:32]([CH3:33])[C:31](S)=[N:30][N:29]=4)[OH:27])[CH:24]=3)[N:19]=[C:18]([O:42][CH3:43])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1>O.C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([C:35]4[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=4)([C:28]4[N:32]([CH3:33])[CH:31]=[N:30][N:29]=4)[OH:27])[CH:24]=3)[N:19]=[C:18]([O:42][CH3:43])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 944Nitric AcidHCID 23668193Sodium NitriteHCID 178487442HCID 178487442、化合物

生成物 1

HCID 210820484-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-alpha-(4-methyl-4H-1,2,4-triazol-3-yl)-6-quinolinemethanol収率 9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium nitrite (0.0095 mol) was added at −70° C. to a solution of nitric acid (10 ml) in water (10 ml). A solution of intermediate (57) (0.0095 mol) in THF (35 ml) was added dropwise carefully. The mixture was stirred at room temperature for 15 minutes, then poured out into ice water, extracted with DCM and washed with potassium carbonate 10%. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 3.8 g (61%). A sample (0.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.42 g of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-methoxy-α-(4-methyl-4H-1,2,4-triazol-3-yl)-6-quinolinemethanol, mp. 155° C. (intermediate 58).

後処理

  1. extractionextracted with DCM
  2. washwashed with potassium carbonate 10%
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customyielding 3.8 g (61%)
  11. customA sample (0.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm)
  12. customThe pure fractions were collected
  13. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-4c6d7d1bc0de415f97347c998a265d91
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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