Water → HCID 57599641, compound

HRID 1091520Notes

Reaction equation

HRID 1091520 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].[CH3:15][O:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:13][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:15][O:16][CH3:17])[C:6]#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 70592654-hydroxy-3-methoxy-2-nitrobenzonitrile

Product 1

HCID 57599641HCID 57599641, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-hydroxy-3-methoxy-2-nitrobenzonitrile 1.00 g, chloromethyl methyl ether 0.47 mL (6.18 mmol) and potassium carbonate 3.56 g (25.8 mmol) in N,N-dimethylformamide 10 mL was stirred at 50° C. for 2 hours. The reaction mixture was poured into water and extracted into diethyl ether. The organic layer was washed with brine, dried over MgSO4, filtrated and the solvent was evaporated. Silica gel chromatography (n-hexane/AcOEt=4/1) afforded the title compound 1.03 g as colorless solid. Yield 83.5%.

Workup

  1. extractionextracted into diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-33128000e6644a1988e875d9139a3afc
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

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