Methyl 2-nitroacetate → 4-(5-Benzyloxy-2-nitrophenyl)-5-dimethylamino-2-nitro-2,4-pentadienoic acid methylester

HRID 127507

Reaktionsgleichung

Reaktionsgleichung von HRID 127507
[CH3:1][N:2]([CH3:24])[CH:3]=[C:4]([C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22])[CH:5]=O.[N+:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])([O-:27])=[O:26]>C(OC(=O)C)(=O)C>[CH3:32][O:31][C:29](=[O:30])[C:28]([N+:25]([O-:27])=[O:26])=[CH:5][C:4]([C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22])=[CH:3][N:2]([CH3:24])[CH3:1]

Komponenten

4

Edukt 2

HCID 17206Methyl 2-nitroacetateHCID 544505983-Dimethylamino-2-(5-benzyloxy-2-nitrophenyl)acrolein

Produkt 1

HCID 539081884-(5-Benzyloxy-2-nitrophenyl)-5-dimethylamino-2-nitro-2,4-pentadienoic acid methylesterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A mixture of 17.3 g (0.053 mol) of the compound of Example 40 and 6.3 g (0.53 mol) of methyl nitroacetate in 115 ml of acetic anhydride was heated at 95° for 1 hour. The mixture was concentrated, the residue slurried with ether, filtered and washed with ether to give 17.6 g (78%) of red orange crystals, m.p. 158°-165°. Recrystallization from benzene-dimethylformamide afforded 13.4 g (59%) of product, m.p. 179°-181°.

Aufarbeitung

  1. temperaturewas heated at 95° for 1 hour
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered
  4. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-09d82f8022bb41b18bd1a70ea39bd1ad
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256641

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