Isopropyl iodide → 2-Isopropylamino-4,5-dimethoxy-benzonitrile

HRID 445148

Reaction equation

HRID 445148 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].I[CH:21]([CH3:23])[CH3:22]>[Cu]>[CH:21]([NH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]#[N:5])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 7359672-Amino-4,5-dimethoxybenzonitrile

Product 1

HCID 601128252-Isopropylamino-4,5-dimethoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
90 °C

Procedure

A suspension of 4.52 g (25.4 mmol) 2-amino-4,5-dimethoxy-benzonitrile, 4.38 g (31.7 mmol) potassium carbonate and 100 mg copper powder in 15 ml 2-iodo-propane is stirred at 90° C. for 5 days. Extractive work-up with ethyl acetate/water and concentration i.V. affords a dark oil, which is purified by flash chromatography (ethyl acetate/hexane). yield: 4.15 g (74%) yellow oil.

Workup

  1. concentrationExtractive work-up with ethyl acetate/water and concentration i.V
  2. customaffords a dark oil, which
  3. customis purified by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-55a58d2306c7437e944ba3e9a8eac496
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Linked notes

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