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

HRID 1740959Notes

Reaction equation

HRID 1740959 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 98556396-amino-4-methyl-2-PyridinebutanamineYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1c941c45f414472394e42377c78e1718
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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