HCID 67291098、化合物 → HCID 67291611、化合物

HRID 1036932ノート

反応式

HRID 1036932 の反応式
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[CH2:3]1>[Cl-].[NH4+].C(O)C.[Fe]>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH2:3]1

参加物

5

反応物 1

HCID 67291098HCID 67291098、化合物

生成物 1

HCID 67291611HCID 67291611、化合物収率 91%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a suspension of 4,4,6-trimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (12.3 g, 40 mmol) in saturated aqueous ammonium chloride and ethanol (100 mL) was added powder iron (9.3 g, 160 mmol) at room temperature. After addition, the resulting mixture was stirred at reflux under nitrogen for 3 h. The reaction mixture was cooled to room temperature; and filtered through a pad of celite. The solvent of ethanol in filtrate was removed under reduced pressure and the water phase was extracted with ethyl acetate. The combined organic phase was dried, concentrated to give 2-(4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (9.7 g). The product was used in the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 267.1.

後処理

  1. additionAfter addition
  2. temperatureat reflux under nitrogen for 3 h
  3. filtrationand filtered through a pad of celite
  4. customThe solvent of ethanol in filtrate was removed under reduced pressure
  5. extractionthe water phase was extracted with ethyl acetate
  6. customThe combined organic phase was dried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6ed4a23f7ebd4e498feb274e26b726ab
出典データセット
uspto-grants-2013_10
特許番号
US08546427B2

反応ノート

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