Acetic Acid → Isopropyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-phenyl-quinolin-8-yl)-pyridine-5-carboxylate

HRID 2372827Notes

Reaction equation

HRID 2372827 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([CH:17]=O)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:19]([CH2:22][C:23](=O)[CH3:24])([O-:21])=[O:20].[NH2:26]/[C:27](/[CH3:32])=[CH:28]\[C:29]([O-:31])=[O:30].[C:33](O)(=O)[CH3:34].[CH2:37](O)C>>[CH3:24][C:23]1[NH:26][C:27]([CH3:32])=[C:28]([C:29]([O:31][CH:33]([CH3:34])[CH3:37])=[O:30])[CH:17]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15]3)[C:22]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 702EthanolHCID 662962-Propanone, 1-nitro-HCID 151703302-Phenyl-quinoline-8-aldehydeHCID 222503863-Aminocrotonate

Product 1

HCID 15170353Isopropyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-phenyl-quinolin-8-yl)-pyridine-5-carboxylate

Procedure

1.17 g (5 mmol) of 2-phenyl-quinoline-8-aldehyde are boiled in 10 ml of ethanol with 0.9 g (8.75 mmol) of nitroacetone, 0.72 g (5 mmol) of ispropyl 3-aminocrotonate and 0.3 ml (5 mmol) of acetic acid for 1 hour. The precipitated crystals are filtered with suction after cooling and washed with ethanol. 1.1 g of orange-colored crystals of melting point 205° C. are obtained.

Workup

  1. filtrationThe precipitated crystals are filtered with suction
  2. temperatureafter cooling
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-102637f6d5244a568f4e6546ce502758
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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