Acetic Acid → HCID 22642381, compound

HRID 478124Notes

Reaction equation

HRID 478124 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.) in 420 ml of ethanol was refluxed. Upon 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 L of ethyl acetate. While stirring, 138 ml of HCl conc. (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 (i.e. 72% versus 117 g theor.)

Workup

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

Sources & evidence

ORD record
ord-612bc45ba1084c6ab30aad71309f48ff
Source dataset
uspto-grants-2003_11
Patent number
US06641970B2

Reaction notes

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