Water → 1-{4-[4-(2-Hydroxyethyl)anilino]-3-nitrophenyl}ethanone

HRID 724073

Reaction equation

HRID 724073 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+].O>CN(C=O)C>[OH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 669044-Aminophenethyl alcoholHCID 795964'-Chloro-3'-nitroacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 218759851-{4-[4-(2-Hydroxyethyl)anilino]-3-nitrophenyl}ethanoneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-5-acetylnitrobenzene (Oelschlaeger, H.; Schreiber, O. Liebigs Ann. Chem., 1961, 641, 81., 2 g, 10 mmol), 4-aminophenylethyl alcohol (1.64 g, 12 mmol) and NaHCO3 (1 g, 12 mmol) in DMF (60 mL) was heated at 150° C. for 3 h. After cooling, the mixture was poured into water (100 mL) and extracted with ethyl acetate (300 mL). The organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL), then dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 1.36 g (45%) of the title compound as an orange oil; 1H-NMR (CDCl3) δ 9.83 (1H, br.s), 8.20 (1H, d, J=2.1 Hz), 7.94 (1H, dd, J=2.1 Hz, 9.3 Hz), 7.34 (2H, d, J=8.2 Hz), 7.24 (2H, d, J=8.2 Hz), 7.16 (1H, d, J=9.3 Hz), 3.91 (2H, t, J=6.6 Hz), 2.92 (2H, t, J=6.6 Hz), 2.57 (3H, s).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1928c56af774416dbbf55fd909b475a9
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Linked notes

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