Ammonium Chloride → 2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)aniline

HRID 12383

反応式

HRID 12383 の反応式
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH2:4][CH2:3]1.[NH4+].[Cl-]>CO.[Zn]>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 574233104,4-Dimethyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 593377072-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)aniline収率 73%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

The crude 1c (0.66 g) was stirred in MeOH (20 mL) at rt. Solid NH4Cl (0.62 g) was added, followed by addition of Zn dust (3.0 g) portionwise. The resulting mixture was stirred at rt for 2 h. It was filtered through Celite®, rinsed with CH2Cl2, and concentrated to dryness. The residue was purified by flash chromatography (hexanes/EtOAc) to give pure amine 1d (0.43 g, 73% for two steps). LC-MS ESI 253 (M+H).

後処理

  1. filtrationIt was filtered through Celite®
  2. washrinsed with CH2Cl2
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash chromatography (hexanes/EtOAc)

出典と根拠

ORDレコード
ord-2a90426445fb4e3f9d543bc95254b264
出典データセット
uspto-grants-2010_06
特許番号
US07728008B2

関連ノート

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