3-Chloro-2-methylaniline → Quinoline

HRID 2290603Notes

Reaction equation

HRID 2290603 reaction equation
C(C(C=C)=O)C.ClC1C(C)=C(C=CC=1)N.C([C:18]1[CH:19]=[N:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23](Cl)[C:22]=2C)C.C(C1CC2C(=C(C)C(Cl)=CC=2)NC1)C>>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 68943-Chloro-2-methylanilineHCID 153941-Penten-3-oneHCID 202315817-Chloro-3-ethyl-1,2,3,4-tetrahydro-8-methylquinolineHCID 20231582HCID 20231582, compound

Product 1

HCID 7047QuinolineYield 60%

Procedure

The procedure described in Example 1 was followed, except that 187 g/hour of ethylacrolein and 283 g/hour of 3-chloro-2-methylaniline were employed. Distillation gave 335 g of distillate at a boiling point of 125° C./2 mm Hg. This distillate contained 75% by weight of 3-ethyl-7-chloro-8-methylquinoline and 22% by weight of 3-ethyl-7-chloro-8-methyltetrahydroquinoline, corresponding to a quinoline yield of 60%, based on 3-chloro-2-methylaniline employed.

Workup

  1. distillationDistillation
  2. customgave 335 g of distillate at a boiling point of 125° C./2 mm Hg

Sources & evidence

ORD record
ord-8b63cdd7c5674eae8cf7d3b1873c5730
Source dataset
uspto-grants-1986_10
Patent number
US04617395

Reaction notes

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