1,2-Dichloroethane → 2-(2-Chloro-ethoxy)-6-nitro-phenylamine

HRID 581698Notes

Reaction equation

HRID 581698 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].[Cl:12][CH2:13][CH2:14]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:12][CH2:13][CH2:14][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

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamineYield 84.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A slurry containing 2-amino-3-nitrophenol (32.0 g, 0.208 mol), 1,2-dichloroethane (260.0 g, 2.65 mol), potassium carbonate (35.0 g, 0.252 mol) and 2-butanone (750 mL) was refluxed for 24 hr. The mixture was cooled, filtered and the solids were washed with ethyl acetate. The filtrate was concentrated to an oily residue that was dissolved in ethyl acetate (500 mL). The organic layer was washed with 1 N sodium hydroxide (250 mL), water (500 mL), and brine (2×500 mL), dried over anhydrous magnesium sulfate. Concentration of the filtered solution and trtuation of the residue with hexane afforded 37.8 g (84.6%) of product as an orange solid, mp 71-73° C.; MS (+)PBEI m/e 216/218 (M+).

Workup

  1. temperaturewas refluxed for 24 hr
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solids were washed with ethyl acetate
  5. concentrationThe filtrate was concentrated to an oily residue that
  6. dissolutionwas dissolved in ethyl acetate (500 mL)
  7. washThe organic layer was washed with 1 N sodium hydroxide (250 mL), water (500 mL), and brine (2×500 mL)
  8. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-364b2e73e3df49b298911dc5f183f23a
Source dataset
uspto-grants-1999_07
Patent number
US05922715

Reaction notes

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