Benzene → 3-(2-Amino-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester

HRID 1976894Notes

Reaction equation

HRID 1976894 reaction equation
C1C=CC=CC=1.[CH2:7]([O:9][C:10](=[O:27])[C:11]([CH3:26])=[CH:12][C:13]1[CH:18]=[C:17]2[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:16]2=[CH:15][CH:14]=1)[CH3:8]>[Fe].O>[CH2:7]([O:9][C:10](=[O:27])[C:11]([CH3:26])=[CH:12][C:13]1[CH:18]=[C:17]2[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:16]2=[CH:15][CH:14]=1)[CH3:8]

Participants

5

Reactant 2

HCID 241BenzeneHCID 702149343-(2-Nitro-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester

Product 1

HCID 702169223-(2-Amino-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl esterYield 78.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Into 30 ml of benzene, 2.0 g (7 mmol) of 3-(2-nitro-benzo[d]phenyl)-2-methyl-2-propenoic acid ethyl ester were dissolved; and, with 1.73 g of iron powder (Koso Chem. Co.) and 2.5 ml of distilled water being added thereto under stirring at room temperature, temperature was raised, so that a reaction was carried out for 1.5 hours at 70° C. After the completion of the reaction, insoluble matters were filtered out, and the filtrate was added to 100 ml of water. The resulting solution was extracted twice with 100 ml of ethyl acetate; and thus obtained ethyl acetate solution was successively washed with water, an aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. The washed solution was dried on sodium sulfate anhydride; and, after sodium sulfate was filtered out, the filtrate was concentrated. Thus obtained oily product was refined by a silica gel column chromatography (silica gel; developing solvent: ethyl acetate/hexane=1/5), whereby 1.4 g of the aimed compound were obtained as an oily product (yield: 77%).

Workup

  1. temperaturetemperature was raised, so that a reaction
  2. customAfter the completion of the reaction, insoluble matters
  3. filtrationwere filtered out
  4. additionthe filtrate was added to 100 ml of water
  5. extractionThe resulting solution was extracted twice with 100 ml of ethyl acetate
  6. washand thus obtained ethyl acetate solution was successively washed with water
  7. customThe washed solution was dried on sodium sulfate anhydride
  8. filtrationand, after sodium sulfate was filtered out
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c881ce96a9bb4e4aa098ef1162370d51
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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