Acetic Acid → HCID 22642381, compound

HRID 2414710Notes

Reaction equation

HRID 2414710 reaction equation
[CH3:1][C:2](=[CH2:15])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)=[O:4].C(O)(=O)C.C(OCC)(=O)C.[ClH:26]>C(O)C.[Fe]>[ClH:26].[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:15])=[CH2:1])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 133964192-Methyl-N-(4-nitrophenyl)prop-2-enamide

Product 1

HCID 22642381HCID 22642381, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 114 g of 2-methyl-N-(4-nitro phenyl) acrylamide (0.55 mol) and 92.6 g of Fe powder (1.65 mol=3 mol equiv.) was refluxed in 420 ml of ethanol. While refluxing, 400 ml of acetic acid (6.6 mol=12 mol equiv.) was added. A proper cooling and a safe gas separation were ensured. During the first reaction step a very strong exothermic gas release occurred. After completing of the addition of acetic acid, stirring while refluxing was continued for 60 min. After TLC inspection, 300 ml of ethyl acetate was added and the Fe salts were suction-filtered. The salts were then washed with 1.9 liter of ethyl acetate. While stirring, 138 ml of concentrated HCl (1.65 mol=3 equiv.) was added to the filtrate. The mixture was cooled to 5° C. while stirring. The precipitate was suction-filtered and washed with ethyl acetate. After drying at 40° C., 85 g of N-(4-amino phenyl)-2-methyl acrylamide hydrochloride was obtained.

Workup

  1. temperatureWhile refluxing
  2. temperatureA proper cooling
  3. customa safe gas separation
  4. customDuring the first reaction step a very strong exothermic gas release
  5. temperaturewhile refluxing
  6. filtrationthe Fe salts were suction-filtered
  7. washThe salts were then washed with 1.9 liter of ethyl acetate
  8. stirringWhile stirring
  9. stirringwhile stirring
  10. filtrationThe precipitate was suction-filtered
  11. washwashed with ethyl acetate
  12. customAfter drying at 40° C.

Sources & evidence

ORD record
ord-34a49608631d46cdb6fed43d99ceb652
Source dataset
uspto-grants-2004_11
Patent number
US06815139B2

Reaction notes

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