4-Nitrobenzaldehyde → HCID 54172310, compound

HRID 322169Notes

Reaction equation

HRID 322169 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([CH2:16][C:17]([O:19][CH2:20][CH2:21][C:22]#[N:23])=[O:18])(=[O:15])[CH2:13][CH3:14]>CC(O)C.N1CCCCC1.C(O)(=O)C>[C:22]([CH2:21][CH2:20][O:19][C:17](=[O:18])[C:16](=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:12](=[O:15])[CH2:13][CH3:14])#[N:23]

Participants

6

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 22725151HCID 22725151, compound

Product 1

HCID 54172310HCID 54172310, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of 4-nitrobenzaldehyde (18.3 g, 0.118 mol), 2-cyanoethyl propionylacetate (20.0 g, 0.118 mol), piperidine (503 mg, 5.91 mmol) and acetic acid (355 mg, 5.91 mmol) in 230 ml of 2-propanol was stirred at r.t. for 48 hrs. Reaction mixture was filtered, the solid collected was dried in air to give 2-[(4-nitrophenyl)methylene]-3-oxopentanoic acid 2-cyanoethyl ester as a white powder (31.7 g, 89%). A solution of 2-[(4-nitrophenyl)methylene]-3-oxopentanoic acid 2-cyanoethyl ester (14.72 g, 48.7 mmol) and benzyl 3-aminocrotonate (10.00 g, 48.7 mmol) in 150 ml of EtOH was refluxed for 36 hrs. After solvent was removed, the residue was dissolved in 250 ml of CHCl3 washed with water (2×100 ml) and dried over Na2SO4. After filtration and removal of solvent, 3-benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (23.0 g, 96%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered
  3. customthe solid collected
  4. customwas dried in air

Sources & evidence

ORD record
ord-2303b6551480455a95df54dab5a79c24
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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