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

HRID 2269776Notes

Reaction equation

HRID 2269776 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].O>[Fe].C(OCC)(=O)C.CCCCCC>[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

6

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 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 21226206Ethyl acetate hexaneSolvent

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 the mixture was heated to 70° C. After a reaction of 1.5 hours, insoluble matters were filtered out. The filtrate was added to 100 ml of water, and then was extracted twice with 100 ml of ethyl acetate. The resulting ethyl acetate solution was successively washed with water, an aqueous sodium hydrogencarbon ate solution, and a saturated aqueous sodium chloride solution. The washed product was dried on sodium sulfate anhydride and concentrated, whereby an oily product was obtained. This 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 the mixture
  2. temperaturewas heated to 70° C
  3. customAfter a reaction of 1.5 hours, insoluble matters
  4. filtrationwere filtered out
  5. additionThe filtrate was added to 100 ml of water
  6. extractionwas extracted twice with 100 ml of ethyl acetate
  7. washThe resulting ethyl acetate solution was successively washed with water
  8. customThe washed product was dried on sodium sulfate anhydride
  9. concentrationconcentrated
  10. customwhereby an oily product was obtained

Sources & evidence

ORD record
ord-6caa2bbe18ad4d7698902dbd1ace6ab2
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

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