Hydroxyamine hydrochloride → HCID 21834436, compound

HRID 1740957Notes

Reaction equation

HRID 1740957 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([N:11]2C(C)=CC=C2C)[CH:8]=[C:7]([CH3:18])[CH:6]=1)[CH2:2][CH:3]=[CH2:4].Cl.NO.C(OCC)(=O)C.ClCCl>C(O)C.O.C(OCC)C>[NH2:11][C:9]1[CH:8]=[C:7]([CH3:18])[CH:6]=[C:5]([CH2:1][CH2:2][CH:3]=[CH2:4])[N:10]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 21226138Dichloromethane ethylacetateHCID 21834427HCID 21834427, compound

Product 1

HCID 21834436HCID 21834436, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 147 mg (0.612 mmol) of 6-(3-buten-1-yl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine and 215 mg (3.09 mmol) of hydroxylamine hydrochloride in 1.6 mL of 95% ethanol and 0.6 mL of water was heated overnight in a 100° C. oil bath. After cooling to room temperature, the solution was diluted with 25 mL of ethyl ether and washed with 15 mL of 2.5 N aqueous sodium hydroxide followed by 15 mL of saturated aqueous sodium chloride. The aqueous layers were extracted in succession with 25 mL of ethyl ether. The combined ethyl ether layers were dried (sodium sulfate), decanted, and evaporated. Flash column chromatography on 6 g of silica gel eluting with 100 mL of 1:1 ethyl acetate/dichloromethane gave 82 mg (83% yield) of 2-amino-6-(3-buten-1-yl)-4-methylpyridine as a pale yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 15 mL of 2.5 N aqueous sodium hydroxide
  3. extractionThe aqueous layers were extracted in succession with 25 mL of ethyl ether
  4. dry with materialThe combined ethyl ether layers were dried (sodium sulfate)
  5. customdecanted
  6. customevaporated

Sources & evidence

ORD record
ord-93384e65ac8549409e4573534e10d685
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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