Water → 6-amino-4-methyl-2-Pyridinebutanamine

HRID 1740959ノート

反応式

HRID 1740959 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2C(C)=CC=C2C)[N:5]=[C:4]([N:19]2C(C)=CC=C2C)[CH:3]=1.O.Cl.NO.[OH-].[K+]>C(O)C>[NH2:19][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[N:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 218344544-Methyl-2-(2,5-dimethylpyrrol-1-yl)-6-(4-(2,5-dimethylpyrrol-1-yl)butyl)pyridine

生成物 1

HCID 98556396-amino-4-methyl-2-Pyridinebutanamine収率 75%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

4-Methyl-2-(2,5-dimethylpyrrol-1-yl)-6-(4-(2,5-dimethylpyrrol-1-yl)butyl)pyridine (429 mg, 1.28 mmol) was dissolved in 6.5 mL of 95% ethanol and 2.5 mL of water was added followed by 818 mg (11.8 mmol) of hydroxylamine hydrochloride and 450 mg (6.96 mmol) of 87% potassium hydroxide. The mixture was heated in a 100° C. oil bath for 18 h. After cooling the reaction to room temperature, most of the ethanol was removed on a rotary evaporator. The residue was partitioned between 10 mL of 2 N aqueous hydrochloric acid and 20 mL of ethyl ether. The aqueous layer was made strongly basic by the addition of solid 87% potassium hydroxide and then extracted with 3×20 mL of ethyl ether. The combined ethyl ether extracts were dried over potassium hydroxide and sodium sulfate, decanted, and evaporated. The residue was purified by flash column chromatography on 6 g of silica gel eluting with 100 mL of 1% ammonium hydroxide and 7% methanol in dichloromethane followed by 100 mL of 2% ammonium hydroxide and 10% methanol in dichloromethane to give 172 mg (75% yield) of 2-amino-6-(4-aminobutyl)-4-methylpyridine as a light amber oil.

後処理

  1. temperatureAfter cooling
  2. customthe reaction to room temperature
  3. custommost of the ethanol was removed on a rotary evaporator
  4. customThe residue was partitioned between 10 mL of 2 N aqueous hydrochloric acid and 20 mL of ethyl ether
  5. additionThe aqueous layer was made strongly basic by the addition of solid 87% potassium hydroxide
  6. extractionextracted with 3×20 mL of ethyl ether
  7. dry with materialThe combined ethyl ether extracts were dried over potassium hydroxide and sodium sulfate
  8. customdecanted
  9. customevaporated
  10. customThe residue was purified by flash column chromatography on 6 g of silica gel eluting with 100 mL of 1% ammonium hydroxide and 7% methanol in dichloromethane

出典と根拠

ORDレコード
ord-1c941c45f414472394e42377c78e1718
出典データセット
uspto-grants-1999_10
特許番号
US05972975

反応ノート

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