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

HRID 415109Notes

Reaction equation

HRID 415109 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].C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH:19](Cl)[CH3:20]>CC(=O)CC>[Cl:18][CH2:19][CH2:20][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 63651,1-DichloroethaneHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamineYield 70%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-Amino-3-nitrophenol (10.0 g, 64.9 mmol, commercially available from Aldrich) was dissolved in 200 mL 2-butanone, potassium carbonate (18.0 g, 0.13 mol) and dichloroethane (15 mL) were added. The suspension was refluxed for 20 hours. The reaction was allowed to cool to room temperature and filtered through a plug of Celite and the retained solid residue was washed with ethyl acetate. The combined filtrate was concentrated under reduced pressure. The crude material was redissolved in 200 mL of ethyl acetate, washed with water, 1N sodium hydroxide solution water, saturated sodium chloride solution dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure to give 9.8 g of 2-(2-Chloroethoxy)-6-nitroaniline (70% yield), which was used without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.80 (d, 1H), 6.95 (d, 1H), 6.61 (dd, 1H), 6.42 (b, 2H), 4.30 (t, 2H), 3.90 (t, 2H). MS (EI): 217 (MH+).

Workup

  1. temperatureThe suspension was refluxed for 20 hours
  2. filtrationfiltered through a plug of Celite
  3. washthe retained solid residue was washed with ethyl acetate
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. dissolutionThe crude material was redissolved in 200 mL of ethyl acetate
  6. washwashed with water, 1N sodium hydroxide solution water, saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-cf9da9817549418d9e96e9e94c48fdbc
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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