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

HRID 127495

Reaction equation

HRID 127495 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl: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]([Cl: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 538029003-Dimethylamino-2-[4-chloro-2-nitrophenyl]acrolein

Product 1

HCID 541350045-Dimethylamino-2-nitro-4-[4-chloro-2-nitrophenyl]-2,4-pentadienoic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 73.1 g (0.29 mol) of the compound of Example 13, 34.0 g (0.29 mol) of methyl nitroacetate and 600 ml of acetic anhydride was stirred and heated at 90°-95° for 45 minutes. The reaction mixture was allowed to cool to room temperature and the crystalline product was collected by filtration. The filtrate was concentrated in vacuo and the residue was slurried with ether (200 ml.) and filtered. The combined materials were washed with ether and dried to give 91.0 g (89%) of red orange crystals, m.p. 193°-197°. Recrystallization from benzenedimethylformamide (6:1,1725 ml) afforded 78.8 g (77%) of product, m.p. 198°-200°.

Workup

  1. temperatureheated at 90°-95° for 45 minutes
  2. filtrationthe crystalline product was collected by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered
  5. washThe combined materials were washed with ether
  6. customdried

Sources & evidence

ORD record
ord-095bee3a554d4eb387f5578d3b123b6c
Source dataset
uspto-grants-1981_03
Patent number
US04256641

Linked notes

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