Aniline → HCID 178482113, compound

HRID 591220Notes

Reaction equation

HRID 591220 reaction equation
[CH:1](=O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:1]=[N:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7362FurfuralHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 178482113HCID 178482113, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Furfural (A, 580.0 mg, 6.04 mmol) was placed in a round-bottom flask and dissolved in 7.50 mL dichloromethane. Magnesium sulfate (750 mg, 6.23 mmol, 1.03 equiv) was added to it followed by aniline (B, 660 uL, d 1.02 g/mL, 1.23 mmol, 1.20 equiv) and the reaction mixture was stirred at room temperature for 15 hrs. Upon completion, the drying reagent was filtered off and the residual solvent was removed on the rotary evaporator. The product imine C (883.0 mg, 86% yield) was recovered as volatile red-brown oil that was used without further purification. 1H NMR (500 MHz, CDCl3) δ 8.30 (s, 1H), 7.63 (br s, 1H), 7.44-7.36 (m, 2H), 7.30-7.22 (m, 3H), 7.02 (s, 1H), 6.57 (dd, J=3.4, 1.7 Hz, 1H). (1H-NMR: Purity>95%).

Workup

  1. filtrationUpon completion, the drying reagent was filtered off
  2. customthe residual solvent was removed on the rotary evaporator
  3. customThe product imine C (883.0 mg, 86% yield) was recovered as volatile red-brown oil that
  4. customwas used without further purification

Sources & evidence

ORD record
ord-674508a6e64943d6b5d001cdc75a3755
Source dataset
uspto-grants-2016_01
Patent number
US09238654B2

Reaction notes

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