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

HRID 12383

반응식

HRID 12383 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2a90426445fb4e3f9d543bc95254b264
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728008B2

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