2-Methyl-4-nitroaniline → 2-Cyano-3-(2-methyl-4-nitrophenyl)acrylic Acid Ethyl Ester

HRID 612056Notes

Reaction equation

HRID 612056 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.C(O[CH:15]=[C:16]([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[C:16]([C:22]#[N:23])=[CH:15][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1])[CH3:21]

Participants

4

Reactant 2

HCID 74412-Methyl-4-nitroanilineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 543550972-Cyano-3-(2-methyl-4-nitrophenyl)acrylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-4-nitroaniline (38.0 g, 250 mmol), ethyl (ethoxymethylene)-cyanoacetate (50.8 g, 300 mmol), and 200 ml of toluene was refluxed for 24 h, cooled, diluted with 1:1 ether-hexane, and filtered. The resulting white solid was washed with hexane-ether and dried to give 63.9 g, mp 180-210° C.

Workup

  1. temperaturewas refluxed for 24 h
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe resulting white solid was washed with hexane-ether
  5. customdried
  6. customto give 63.9 g, mp 180-210° C.

Sources & evidence

ORD record
ord-0f65c7ca188d43fea82c1e23360867dd
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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