Water → 2-Methyl-5-(2-methyl-1,3-dioxolan-2-yl)aniline

HRID 1893535ノート

反応式

HRID 1893535 の反応式
O.[C:2]1([CH3:8])C=CC=CC=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:18])=[O:17])=[CH:12][C:11]=1[N+:19]([O-])=O.C1(C)C=CC(S(O)(=O)=[O:29])=CC=1>C(O)CO>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH3:18])[O:29][CH2:2][CH2:8][O:17]2)=[CH:12][C:11]=1[NH2:19]

参加物

6

反応物 4

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 792463'-Nitro-4'-methylacetophenone

生成物 1

HCID 668820662-Methyl-5-(2-methyl-1,3-dioxolan-2-yl)aniline収率 94%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

To a flask mounted with Dean-Stark water removing apparatus (Dean-Stark trap) were added toluene (200 ml), 4-methyl-3-nitroacetophenone (9.77 g, 54.53 mmol), ethylene glycol (4.6 ml) and p-toluenesulfonic acid.monohydrate (0.79 g), and the mixture was heated under reflux for 100 min. The reaction mixture was cooled, washed with diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a crude brown oil (13.0 g). Using the crude oil and according to the method of Reference Example 61, step B, the title compound (9.89 g, yield 94%) was obtained as a pale-yellow solid.

後処理

  1. temperatureunder reflux for 100 min
  2. temperatureThe reaction mixture was cooled
  3. washwashed with diluted aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customto give a crude brown oil (13.0 g)

出典と根拠

ORDレコード
ord-9798094bdea14ce180d24232641e453d
出典データセット
uspto-grants-2013_08
特許番号
US08513235B2

反応ノート

読み込み中…