3-Chloroaniline → 7-Chloro-4-methylquinoline

HRID 2299271

반응식

HRID 2299271 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 1704377-Chloro-4-methylquinoline

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ac55fcaeb50643e2b0ba2810ec540d45
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495692B1

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