Hydrochloric Acid → HCID 21834419, compound

HRID 1740962Notes

Reaction equation

HRID 1740962 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2C(C)=CC=C2C)[CH:7]=[C:6]([CH3:17])[CH:5]=1.Cl.NO.[OH-].[K+].Cl>C(O)C.ClCCl.O>[NH2:10][C:8]1[CH:7]=[C:6]([CH3:17])[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[N:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 443297Hydroxyamine hydrochlorideHCID 23506708HCID 23506708, compound

Product 1

HCID 21834419HCID 21834419, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-(2-Hydroxyethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine (457 mg, 1.98 mmol) was dissolved in 5.0 mL of 95% ethanol and 2.0 mL of water was added followed by 625 mg (8.99 mmol) of hydroxylamine hydrochloride and 350 mg (5.36 mmol) of 86% potassium hydroxide. The mixture was heated in a 100° C. oil bath for 24 h, the cooled to room temperature and partitoned between 15 mL of 2 N aqueous hydrochloric acid and 30 mL of dichloromethane. The aqueous layer was made strongly basic by the addition of solid 86% potassium hydroxide and extracted with 3×30 mL of ethyl ether. The ethyl ether layers were dried (sodium sulfate), decanted, and evaporated. The residue was purified by flash column chromatography on 25 g of silica gel, eluting with 20% isopropanol in dichloromethane to give 201 mg (67% yield) of 2-amino-6-(2-hydroxyethyl)4-methylpyridine as a colorless oil which spontaneously crystallized.

Workup

  1. temperaturethe cooled to room temperature
  2. extractionextracted with 3×30 mL of ethyl ether
  3. dry with materialThe ethyl ether layers were dried (sodium sulfate)
  4. customdecanted
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on 25 g of silica gel
  7. washeluting with 20% isopropanol in dichloromethane

Sources & evidence

ORD record
ord-0326daf39085491db0cffa756a12e5aa
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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