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

HRID 1369196Notes

Reaction equation

HRID 1369196 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:9].[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].C([O-])(O)=O.[Na+].C(O)(CC)(C)C>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[OH:14][CH2:13][CH2:12][CH2:11][NH:10][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:9]

Participants

7

Reactant 4

HCID 64052-Methyl-2-butanolHCID 90863-Amino-1-propanolHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 178526251HCID 178526251, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 2-chloropyridine-N-oxide hydrochloride (16.6 g, 0.1 mole), 3-amino-1-propanol (15.3 mL, 0.2 mole), NaHCO3 (42 g, 0.5 mole), and tert-amyl alcohol (100 mL) was heated to reflux. After 21 hr, the reaction was cooled, diluted with CH2Cl2 (300 mL), and suction filtered to remove insoluble materials. The filtrate was concentrated and reconcentrated from toluene to leave a yellow oil. Silica gel chromatography (20% MeOH/CHCl3) gave the title compound (15.62 g, 93%) as a yellow solid: TLC (20% MeOH/CHCl3) Rf0.48; 1H NMR (250, CDCl3) δ8.07 (dd, J=6.6, 1.2 Hz, 1 H), 7.34 (br t, 1 H), 7.10-7.30 (m, 1 H), 6.64 (dd, J=8.5, 1.4 Hz, 1 H), 6.40-6.60 (m, 1 H), 4.49 (br s, 1 H), 3.65-3.90 (m, 2 H), 3.35-3.60 (m, 2 H), 1.75-2.00 (m, 2 H); MS (ES) m/e 169 (M+H)+.

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 leave a yellow oil

Sources & evidence

ORD record
ord-de50cd561cc94f48b8c56be04a12e2a1
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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