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

HRID 2192212

Reaction equation

HRID 2192212 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-766cb1a34b974b689e5e6e5f8a63d2f9
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Linked notes

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