Hydrochloric Acid → 8-Chloro-2-methylquinoline

HRID 26362

Reaction equation

HRID 26362 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:12]([CH3:13])[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 14798Sodium HydroxideHCID 447466Crotonaldehyde

Product 1

HCID 2211138-Chloro-2-methylquinolineYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 128 g (1.0 mole) of o-chloroaniline, 304 g of conc. hydrochloric acid and 61 g of water was maintained at 90°-95° C., and with sufficient stirring, 70 g (1.0 mole) of crotonaldehyde was added dropwise over the course of 2 hours. After the addition, the mixture was reacted further at 90°-95° C. for 1 hour. The reaction mixture was cooled, and then rendered alkaline by adding a conc. aqueous solution containing 132 g of sodium hydroxide with ice cooling. The alkaline mixture was separated into layers, and the oily layer was distilled at 2-3 mmHg to afford 72 g (0.4 mole) of 8-chloroquinaldine.

Workup

  1. temperaturewas maintained at 90°-95° C.
  2. additionAfter the addition
  3. customthe mixture was reacted further at 90°-95° C. for 1 hour
  4. temperatureThe reaction mixture was cooled
  5. additionby adding a conc. aqueous solution
  6. customThe alkaline mixture was separated into layers
  7. distillationthe oily layer was distilled at 2-3 mmHg

Sources & evidence

ORD record
ord-db3bc50b3c8b426bb0e8a16b689b26e4
Source dataset
uspto-grants-1979_04
Patent number
US04150025

Linked notes

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