2-Chlorobenzaldehyde → HCID 13564978, compound

HRID 236571Notes

Reaction equation

HRID 236571 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10]/[C:11](/[CH3:22])=[CH:12]\[C:13]([O:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])=[O:14].[N+:23]([CH2:26][C:27](=O)[CH3:28])([O-:25])=[O:24]>C(O)C>[CH3:28][C:27]1[NH:10][C:11]([CH3:22])=[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])=[O:14])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])[C:26]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 662962-Propanone, 1-nitro-HCID 21278157HCID 21278157, compound

Product 1

HCID 13564978HCID 13564978, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28.1 g (200 mmol) of 2-chlorobenzaldehyde are boiled under reflux with 37.4 g (200 mmol) of 2-acetoxyethyl β-aminocrotonate and 32.6 g (320 mmol) of nitroacetone in 400 ml of ethanol for 4 hours. The mixture is cooled and concentrated. The evaporation residue is taken up in ethyl acetate and the mixture is washed with water, sodium bicarbonate solution and water again, dried and concentrated. The semi-solid evaporation residue is stirred with ethanol, filtered off with suction and washed with ethanol. 23.2 g (29.4% of theory) of a yellow-colored product of melting point 158°-160° C. are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated
  3. washthe mixture is washed with water, sodium bicarbonate solution and water again
  4. customdried
  5. concentrationconcentrated
  6. customThe semi-solid evaporation residue
  7. filtrationfiltered off with suction
  8. washwashed with ethanol
  9. custom23.2 g (29.4% of theory) of a yellow-colored product of melting point 158°-160° C. are obtained

Sources & evidence

ORD record
ord-09dfd876ef0a4019949835f7b55cc85e
Source dataset
uspto-grants-1987_02
Patent number
US04645775

Reaction notes

Loading…