Water → 2-(2-Ethylhexanoylamino)-4-nitrophenol

HRID 849901Notes

Reaction equation

HRID 849901 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12]([CH:14]([CH2:18][CH2:19][CH2:20][CH3:21])[C:15](Cl)=[O:16])[CH3:13].C(Cl)Cl.O>N1C=CC=CC=1>[CH2:12]([CH:14]([CH2:18][CH2:19][CH2:20][CH3:21])[C:15]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11])=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 791032-Ethylhexanoyl chlorideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 193654512-(2-Ethylhexanoylamino)-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

77 g 2-amino-4-nitrophenol were dissolved in 1600 ml pyridine. 81 g 2-ethylhexanoic acid chloride were added at 15 C. over 1 hour and the batch was subsequently heated at 35 C. for 5 hours. 250 ml methylene chloride and 700 ml water were added thereto, and the organic phase was washed with water and dilute hydrochloric acid and dried over Na2SO4, and the solvent was distilled off. The crude product was purified by means of column chromatography (silica gel 60, mobile phase toluene/ethyl acetate (4:1)) and was recrystallised from aqueous ethanol: 39 g of yellow solid with a melting point of 151 to 152 C.

Workup

  1. temperaturethe batch was subsequently heated at 35 C
  2. waitfor 5 hours
  3. washthe organic phase was washed with water and dilute hydrochloric acid
  4. dry with materialdried over Na2SO4
  5. distillationthe solvent was distilled off
  6. customThe crude product was purified by means of column chromatography (silica gel 60, mobile phase toluene/ethyl acetate (4:1))
  7. customwas recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-038831b4d0f74a5ca76caf148ae60524
Source dataset
uspto-grants-2000_01
Patent number
US06015654

Reaction notes

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