Water → 2-(2-Methoxyethoxy)-6-nitroaniline

HRID 18541

Reaction equation

HRID 18541 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14][O:15][CH3:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:16][O:15][CH2:14][CH2:13][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 593496042-(2-Methoxyethoxy)-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g 2-Amino-3-nitro-phenol, 4.5 g 1-Bromo-2-methoxy-ethane, 4.4 g K2CO3 in 50 mL DMF were heated to 60° C. for 16 h. Then 50 mL of water were added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over MgSO4, and the solvents were removed under reduced pressure. The remaining product was pure enough for the next reaction step. Yield: 5.8 g.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe remaining product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-e4212dad419940b0b09a993a75280f66
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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