Ammonium Chloride → (E)-Ethyl 3-(4-aminophenyl)-2-methylacrylate

HRID 2265102Notes

Reaction equation

HRID 2265102 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[C:11](\[CH3:17])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>O.CO.C1COCC1.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[C:11](\[CH3:17])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 11241815Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate

Product 1

HCID 15086587(E)-Ethyl 3-(4-aminophenyl)-2-methylacrylateYield 58.9%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The obtained ethyl 3-(4-nitrophenyl)-2-methylacrylate (3.5 g) was dissolved in a mixed solvent of water (75 ml), methanol (75 ml), and THF (75 ml). Ammonium chloride (3.05 g) and iron powder (4.2 g) were added thereto, and the obtained mixture was stirred at 50° C. for 4 hours. The iron powder was filtered, and the solvent was distilled off under reduced pressure. Methanol was added to the obtained residue, and insoluble substances were filtered off. The filtrate was separated with ethyl acetate and water. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (3% chloroform/methanol) to obtain Compound 13a (1.8 g, 32%) as an orange liquid.

Workup

  1. filtrationThe iron powder was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionMethanol was added to the obtained residue, and insoluble substances
  4. filtrationwere filtered off
  5. customThe filtrate was separated with ethyl acetate and water
  6. washThe organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography (3% chloroform/methanol)

Sources & evidence

ORD record
ord-30719d187006457e9180ad33a1e1adc6
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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