4-Nitrobenzaldehyde → HCID 54056370, compound

HRID 322178Notes

Reaction equation

HRID 322178 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]([CH2:17][C:18]([O:20][CH2:21][CH2:22][C:23]#[N:24])=[O:19])(=[O:16])[CH2:13][CH2:14][CH3:15]>CC(O)C.N1CCCCC1.C(O)(=O)C>[C:23]([CH2:22][CH2:21][O:20][C:18](=[O:19])[C:17](=[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:16])[CH2:13][CH2:14][CH3:15])#[N:24]

Participants

6

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 23004047HCID 23004047, compound

Product 1

HCID 54056370HCID 54056370, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of 4-nitrobenzaldehyde (16.61 g, 110 mmol), 2-cyanoethyl butyrylacetate (19.34 g, 100 mmol), piperidine (430 mg, 5.00 mmol) and acetic acid (300 mg, 5.00 mmol) in 350 ml of 2-propanol was stirred at room temperature for 48 hrs. The reaction mixture was filtered and resulting solid was air dried to give 2-[(4-nitrophenyl)methylene]-3-oxohexanoic acid 2-cyanoethyl ester as a white powder (31.0 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customresulting solid
  3. customdried

Sources & evidence

ORD record
ord-4bdefb9a0ade4d14b797a67a16f08f82
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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