Benzaldehyde → HCID 53633977, compound

HRID 1709731Notes

Reaction equation

HRID 1709731 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]([N:16]=[O:17])[CH2:13][CH2:12][CH2:11]2)(=[O:5])[CH3:4].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(Cl)Cl>O.C(O)C>[C:19]1([CH:18]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]([N:16]=[O:17])[CH2:13][CH2:12][CH2:11]3)=[O:5])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 20074936HCID 20074936, compound

Product 1

HCID 53633977HCID 53633977, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

20 g (0.5 mol) of sodium hydroxide were dissolved in 120 ml of water. A cold solution of 109 g (0.5 mol) of 8-acetyl-1-nitroso-1,2,3,4-tetrahydroquinoline and 53 g (0.5 mol) of benzaldehyde in 300 ml of ethanol was added at 0°-5° C. The mixture was stirred at 10° C. for 1 hour, 600 ml of methylene chloride were then added and the mixture was stirred for 1 hour at 10°-20° C. 500 ml of water were then added, the organic layer was separated, dried, and the solvent was distilled off. 153.5 g of crude 8-(3-phenyl-2-propen-1-on-1-yl)-1-nitroso-1,2,3,4-tetrahydroquinoline were obtained.

Workup

  1. stirringthe mixture was stirred for 1 hour at 10°-20° C
  2. customthe organic layer was separated
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-1ad26bd20bae4f2a918d500556bc20cd
Source dataset
uspto-grants-1990_08
Patent number
US04950759

Reaction notes

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