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

HRID 1872844Notes

Reaction equation

HRID 1872844 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 hours. 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 sequentially with 1N sodium hydroxide (250 ml), water (500 ml) and brine (2×500 ml) and then dried over anhydrous magnesium sulfate. Concentration of the filtered solution and trituration of the residue with hexanes afforded 37.8 g (84.6%) of product as an orange solid: mp 71-73° C.; MS EI m/e 216 (M+).

Workup

  1. temperaturewas refluxed for 24 hours
  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 sequentially with 1N 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-36c951d83a7348a1b12d5dc81ea18f9f
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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