Hydrochloric Acid → 4,5,8-Trimethyl-6-nitroquinoline

HRID 1598646

반응식

HRID 1598646 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([CH3:12])=[CH:5][C:3]=1[NH2:4].Cl.CO[CH2:16][CH2:17][C:18](OC)(OC)[CH3:19].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(O)C>[N+:9]([C:7]1[C:6]([CH3:12])=[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=1)[N:4]=[CH:16][CH:17]=[C:18]2[CH3:19])([O-:11])=[O:10]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189634-Nitro-2,5-xylidineHCID 810844-Methoxybutan-2-one-dimethylacetal

생성물 1

HCID 105606624,5,8-Trimethyl-6-nitroquinoline

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

A mixture of 2,5-dimethyl-4-nitroaniline (0.96 g), ferric chloride hexahydrate (2.50 g), zinc chloride (0.094 g), concentrated hydrochloric acid (0.481 mL), and ethanol (8 mL) is heated to 60° C. 1,3,3-trimethoxybutane (0.73 mL) is added dropwise while the reaction mixture is kept at 60° C. The reaction mixture is heated at reflux overnight and cooled to room temperature. A solution of 10% aqueous sodium hydroxide is added, and the mixture is extracted three times with methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and evaporated to afford a crude product. The crude product is purified by flash chromatography using 25% ethyl acetate in hexane as eluent, providing 6-nitro-4,5,8-trimethylquinoline.

후처리

  1. customis kept at 60° C
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux overnight
  4. temperaturecooled to room temperature
  5. extractionthe mixture is extracted three times with methylene chloride
  6. dry with materialThe combined organic layers are dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a crude product
  10. customThe crude product is purified by flash chromatography

출처 및 근거

ORD 기록
ord-5232e5899cfb43e38c3858ee8996cd17
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739148

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