Carbon Dioxide → HCID 70592850, compound

HRID 27242Notes

Reaction equation

HRID 27242 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]=[C:10]=O.Cl.[C:14](=O)=O.[OH-:17].[Na+].[C:19]([CH2:22][C:23](=O)C)(=[O:21])C>O>[C:22]([C:19]1([OH:21])[CH:2]=[C:3]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]2)=[N:9][CH:10]1[CH3:14])(=[O:17])[CH3:23]

Participants

7

Reactant 5

HCID 280Carbon Dioxide2×HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31261AcetylacetoneHCID 12413922HCID 12413922, compound

Product 1

HCID 70592850HCID 70592850, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

38.4 g (0.19 mol) of 2-dichloromethyl-phenyl isocyanate are allowed to run into a suspension of 135 g (0.43 mol) of Ba(OH)2 ×8H2O in 500 ml of water, at 15°-18° C. whilst stirring vigorously (with the aid of a baffle and an impeller stirrer). The mixture is stirred for a further 30-40 minutes at this temperature and about 95 ml of 10% strength hydrochloric acid are added dropwise to the reaction mixture, at 3°-5° C., until the pH is 5-6, CO2 being evolved. After the evolution of CO2 has subsided, the reaction mixture is rendered alkaline with 4 ml of 50% strength NaOH. After removing the external cooling bath, 25 g (0.25 mol) of acetylacetone are then allowed to run in dropwise in the course of 15-30 minutes and the mixture is stirred for a further 4-6 hours at room temperature. It is then filtered and the filter residue is taken up in methanol and warmed to 40° C. After cooling, the undissolved barium salt is filtered off and the filtrate is evaporated. After drying in a desiccator, 33 g (94% of theory) of 3-acetyl-3-hydroxy-quinaldine with a melting point of 54°-56° C. are obtained.

Workup

  1. customdropwise in the course of 15-30 minutes
  2. stirringthe mixture is stirred for a further 4-6 hours at room temperature
  3. filtrationIt is then filtered
  4. temperatureAfter cooling
  5. filtrationthe undissolved barium salt is filtered off
  6. customthe filtrate is evaporated
  7. customAfter drying in a desiccator

Sources & evidence

ORD record
ord-6f81b4f6fca2443abd1a1a0498cdccda
Source dataset
uspto-grants-1980_09
Patent number
US04220779

Reaction notes

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