2-Methyl-2-butanol → HCID 178526251, compound

HRID 497547

Reaction equation

HRID 497547 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[NH2:9][CH2:10][CH2:11][CH2:12][OH:13].C([O-])(O)=O.[Na+].C(O)(CC)(C)C>C(Cl)Cl>[OH:13][CH2:12][CH2:11][CH2:10][NH:9][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

6

Reactant 4

HCID 64052-Methyl-2-butanolHCID 90863-Amino-1-propanolHCID 754652-Chloropyridine oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 178526251HCID 178526251, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
67 °C

Procedure

A mixture of 2-chloropyridine-N-oxide (16.6 g, 100 mmoles), 3-amino-1-propanol (15.3 ml, 200 mmoles), NaHCO3 (42 g, 0.5 mole), and tert-amyl alcohol (100 ml) was heated to reflux. After 23 hours, the reaction was cooled, diluted with CH2Cl2 (300 ml), and filtered to remove insoluble materials. The filtrate was concentrated to afford a brown oil. The oil was dried under vacuum overnight. Ether (100 ml) was added to give a brown solid. The ether was decanted and the solid was washed further with ether/acetonitrile (3/1). The resulting solid was heated at 67° C. under vacuum to give the desired product (13.5 g). 1H NMR was consistent with the proposed structure.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. concentrationThe filtrate was concentrated
  6. customto afford a brown oil
  7. customThe oil was dried under vacuum overnight
  8. additionEther (100 ml) was added
  9. customto give a brown solid
  10. customThe ether was decanted
  11. washthe solid was washed further with ether/acetonitrile (3/1)

Sources & evidence

ORD record
ord-7638cfb683b8452eb81dd8e69519514f
Source dataset
uspto-grants-2005_09
Patent number
US06949578B2

Linked notes

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