4-Nitroaniline → 2-Methyl-N-(4-nitrophenyl)prop-2-enamide

HRID 2414709Notes

Reaction equation

HRID 2414709 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[N+:7]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)([O-:9])=[O:8].C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:4][C:2](=[CH2:3])[C:1]([NH:14][C:13]1[CH:15]=[CH:16][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)=[O:5]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 10340Sodium CarbonateHCID 13528Methacryloyl chloride

Product 1

HCID 133964192-Methyl-N-(4-nitrophenyl)prop-2-enamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

275 ml of methacryloyl chloride (2.75 mol=1.1 equiv.) was added dropwise to a cooled suspension of 345 g of 4-nitro aniline (2.5 mol) and 290 g of Na2CO3 (2.75 mol =1.1 equiv.) in 2.5 liter acetone. After completing the addition, stirring was continued for 30 min at 30° C. After TLC inspection the reaction mixture was poured into 15 liter of ice-water under stirring. The precipitate was suction-filtered and washed 3 times with 2.5 liter of demineralised water. After drying at 50° C., 476.5 g of 2-methyl-N-(4-nitro phenyl) acrylamide was obtained.

Workup

  1. additionthe addition
  2. stirringunder stirring
  3. filtrationThe precipitate was suction-filtered
  4. washwashed 3 times with 2.5 liter of demineralised water
  5. customAfter drying at 50° C.

Sources & evidence

ORD record
ord-4a09bbaf678a4874a5ca2f2cbf824336
Source dataset
uspto-grants-2004_11
Patent number
US06815139B2

Reaction notes

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