Methyl 2-nitroacetate → 5-Dimethylamino-2-nitro-4-[4-methyl-2-nitrophenyl]-2,4-pentadienoic acid methyl ester

HRID 127496Notes

Reaction equation

HRID 127496 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])[CH:5]=O.[N+:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])([O-:20])=[O:19]>C(OC(=O)C)(=O)C>[CH3:25][O:24][C:22](=[O:23])[C:21]([N+:18]([O-:20])=[O:19])=[CH:5][C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])=[CH:3][N:2]([CH3:17])[CH3:1]

Participants

4

Reactant 2

HCID 17206Methyl 2-nitroacetateHCID 536886483-Dimethylamino-2-[4-methyl-2-nitrophenyl]acrolein

Product 1

HCID 538618625-Dimethylamino-2-nitro-4-[4-methyl-2-nitrophenyl]-2,4-pentadienoic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 67.5 g (0.29 mol) of the compound of Example 15 and 34.3 g (0.29 mol) of methyl nitroacetate in 540 ml of acetic anhydride was heated at 60° for 2 hours. The product was worked up and recrystallized from benzene-DMF (3:1) affording 75.1 g (78%) of product as red orange crystals, m.p. 213°-215°.

Workup

  1. temperaturewas heated at 60° for 2 hours
  2. customrecrystallized from benzene-DMF (3:1)

Sources & evidence

ORD record
ord-322c02f2188e442ca2e0dd6c6fcd1e21
Source dataset
uspto-grants-1981_03
Patent number
US04256641

Reaction notes

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