Hydrochloric Acid → HCID 12394366, compound

HRID 1399939

Reaction equation

HRID 1399939 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CCO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 5354136Methyl (2E)-3-(3-nitrophenyl)-2-propenoate

Product 1

HCID 12394366HCID 12394366, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of (E)-methyl 3-(3-nitrophenyl)acrylate (20.14 g, 0.097 mol), Fe (32.5 g, 0.58 mol), concentrated HCl (3.5 ml) in 50% EtOH (100 ml) was refluxed for 2 h. Upon completion, the solution was filtered through Celite and washed with EtOH. The filtrate was concentrated and extracted with dichloromethane. The combined organic phase was dried over MgSO4 and concentrated to afford (E)-methyl 3-(3-aminophenyl)acrylate as a yellow solid (9.73 g, 57%).

Workup

  1. filtrationUpon completion, the solution was filtered through Celite
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phase was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c4c6ac0849a543009493f1c2594735b1
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Linked notes

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