Chloromethyl Methyl Ether → HCID 66790223, compound

HRID 1672286Notes

Reaction equation

HRID 1672286 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 no) 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-7ccf6b364b244b3caf8a447a4d6240a1
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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