N-(2-Methylbut-3-yn-2-yl)aniline → 2,2-Dimethyl-1,2-dihydroquinoline

HRID 351582Notes

Reaction equation

HRID 351582 reaction equation
[CH3:1][C:2]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])[C:3]#[CH:4]>C1(C)C=CC=CC=1>[CH3:5][C:2]1([CH3:1])[CH:3]=[CH:4][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1

Participants

3

Reactant 1

HCID 345768N-(2-Methylbut-3-yn-2-yl)aniline

Product 1

HCID 124373012,2-Dimethyl-1,2-dihydroquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-[3,3-dimethylpropyn-3-yl]aniline and cuprous chloride (3.9 g) in toluene (140 mL) was refluxed under nitrogen for 4½ hrs. The reaction mixture was filtered and the filtrate washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane:hexane (1:1) to provide the desired compound.

Workup

  1. temperaturewas refluxed under nitrogen for 4½ hrs
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with dichloromethane:hexane (1:1)

Sources & evidence

ORD record
ord-0000ffaeb8334ca7a13303bf76c5bffa
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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