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

HRID 1901464

反応式

HRID 1901464 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f54c31b105564ebf9ec27a26c5c28f03
出典データセット
uspto-grants-1996_11
特許番号
US05578607

関連ノート

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