1-Butanol → 4-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

HRID 1720273ノート

反応式

HRID 1720273 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH2:14](N)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(O)CCC.Cl>CO>[OH2:12].[ClH:1].[CH2:27]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

参加物

6

反応物 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 16217TetradecylamineHCID 7715204-Chloro-2-methylquinolin-6-ol

生成物 1

HCID 224179544-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 150 mg (0.78 mmol) of 4-chloro-2-methylquinolin-6-ol, 174 mg (0.81 mmol) of n-tetradecylamine, and 5 mL of n-butanol was heated under reflux for 24 hours. Excess butanol was removed by codistillation with cyclohexane. The residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane) to furnish crude product. This was taken up in methanol, and the solution was treated with dry hydrogen chloride gas. The solution was evaporated under reduced pressure to give the title compound as crystalline material: m.p. 180°-183° C.

後処理

  1. temperatureunder reflux for 24 hours
  2. customExcess butanol was removed by codistillation with cyclohexane
  3. customThe residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane)
  4. customto furnish crude product
  5. customThe solution was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-340b3e54260d4e0587106922691e4d8e
出典データセット
uspto-grants-1996_04
特許番号
US05506235

反応ノート

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