3-Chloroaniline → 7-Chloro-4-methylquinoline

HRID 2299271

Reaction equation

HRID 2299271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CO[CH2:11][CH2:12][C:13](OC)(OC)[CH3:14]>[Cl-].[Zn+2].[Cl-].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:13]([CH3:14])=[CH:12][CH:11]=[N:5]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 79323-ChloroanilineHCID 810844-Methoxybutan-2-one-dimethylacetal

Product 1

HCID 1704377-Chloro-4-methylquinoline

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

To a mixture containing 3-chloroaniline (1.59 g), ferric chloride hexahydrate (5.4 g), zinc chloride (0.2 g), ethanol (20 ml of 95% aqueous solution) preheated to 60° C. was added 1,3,3-trimethoxybutane (1.48 g). The resulting mixture was refluxed for two hours and allowed to stand overnight. The volatile materials were then removed in vacuo and the residue rendered basic with 10% aqueous sodium hydroxide. The resulting mixture was partitioned between water and diethyl ether (3 times). The combined ether layer was dried over magnesium sulfate. Rotary evaporation of the ether solution gave a dark liquid. The liquid was added to a silica gel column and eluted with hexane/ethyl acetate (3:1) to give the desired product as tan crystals.

Workup

  1. custompreheated to 60° C.
  2. temperatureThe resulting mixture was refluxed for two hours
  3. customThe volatile materials were then removed in vacuo
  4. customThe resulting mixture was partitioned between water and diethyl ether (3 times)
  5. dry with materialThe combined ether layer was dried over magnesium sulfate
  6. customRotary evaporation of the ether solution
  7. customgave a dark liquid
  8. additionThe liquid was added to a silica gel column
  9. washeluted with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ac55fcaeb50643e2b0ba2810ec540d45
Source dataset
uspto-grants-2002_12
Patent number
US06495692B1

Linked notes

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