Sodium Hydroxide → 2-Propenoic acid, 3-(4-aminophenyl)-, methyl ester

HRID 351089

Reaction equation

HRID 351089 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.O.O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 2196853-(4-Nitro-phenyl)-acrylic acid methyl ester

Product 1

HCID 30175782-Propenoic acid, 3-(4-aminophenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-(4-nitro-phenyl)-acrylic acid methyl ester (72) (39.54 g, 0.191 mol) and SnCl2.2H2O (220 g, 0.98 mol) in anhydrous ethanol (300 ml) was heated at 50° C. for 1 hour and at 75° C. for 1 hour. The reaction mixture was allowed to cool to 10° C., treated with 20% NaOH solution to pH 8–9, and extracted with ethyl acetate (3×200 ml). The organic extract was washed with saturated NaCl (3×150 ml), dried (MgSO4), and evaporated under reduced pressure. Recrystallization from isopropanol (180 ml) afforded pure title compound in a form of yellowish crystals (17.938 g, 53%). 1H NMR (DMSO-d6, HMDSO), δ: 3.64 (3H, s); 5.73 (2H, s); 6.22 (1H, d, J=16.0 Hz); 6.57 (2H, d, J=8.0 Hz); 7.38 (2H, d, J=8.0 Hz); 7.50 (1H, d, J=16.0 Hz).

Workup

  1. temperatureto cool to 10° C.
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (3×150 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customRecrystallization from isopropanol (180 ml)

Sources & evidence

ORD record
ord-5f45a7a6d0c04984a917d82e78b10aea
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Linked notes

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