Hydrochloric Acid → HCID 21936548, compound

HRID 1241684Notes

Reaction equation

HRID 1241684 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[ClH:9].[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].[Cl-].[Zn+2:16].[Cl-]>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[N:6]=[C:12]([CH3:13])[CH:11]=[CH:10]2.[Cl-:9].[Zn+2:16].[Cl-:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 447466CrotonaldehydeHCID 3007855Zincchloride

Product 1

HCID 21936548HCID 21936548, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
0 °C

Procedure

(Method A) 4-Chloroaniline (2.55 g, 20 mmol), concentrated hydrochloric acid (5 cm3), tetrachloro-1-4-benzoquinone (5.9 g, 20 mmol), and n-butanol (5 cm3) were mixed and heated to reflux giving a yellow suspension. Crotonaldehyde (1.68 g, 24 mmol) in butanol (2 cm3) was added over 1 hr giving a dark brown solution. After a further 30 mins reflux, zinc chloride (0.5M in THF, 40 cm3, 20 mmol) was added in three portions and reflux continued for 20 mins before cooling slowly to 0° C. and standing for 1 hr. The dark solid was filtered off, washed with ether, IPA and THF before drying in vacuo to give 6-chloro-2-methylquinoline hydrochloride/zinc chloride salt (3 g, 10.6 mmol, 62%). See, for example, Song et al., 1993.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customgiving a yellow suspension
  4. customgiving a dark brown solution
  5. temperatureAfter a further 30 mins reflux
  6. temperaturereflux
  7. waitstanding for 1 hr
  8. filtrationThe dark solid was filtered off
  9. washwashed with ether, IPA and THF
  10. custombefore drying in vacuo

Sources & evidence

ORD record
ord-1927acb3b4304f3485c097ad95ad21bb
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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