Chloromethyl Methyl Ether → HCID 66790223, compound

HRID 1929437Notes

Reaction equation

HRID 1929437 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][O:20][CH3:21]>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:20][CH2:21][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 66790223HCID 66790223, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-nitrophenol (4.62 g) in N,N-dimethylformamide (150 mL) was added potassium carbonate (12.44 g), and thereto was added dropwise chloromethylmethylether (2.73 mL). The mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel; solvent; n-hexane/ethyl acetate=2/1) to give [2-(methoxymethoxy)-4-nitrophenyl]amine (4.76 g) as a yellow oil.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel; solvent; n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-0eb790cbcd4e420185c4fc27072b579a
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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