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

HRID 613379

Reaction equation

HRID 613379 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.CO.C(Cl)(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

7

Reactant 4

HCID 64052-Methyl-2-butanolHCID 90863-Amino-1-propanolHCID 754652-Chloropyridine 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 (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) Rf 0.48; 1H NMR (250, CDCl3) δ 8.07 (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-b6960fd79dce4bc0b5a57ced0b12d413
Source dataset
uspto-grants-1999_12
Patent number
US06008213

Linked notes

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