2-Methyl-2-butanol → HCID 178428733, compound

HRID 2416696Notes

Reaction equation

HRID 2416696 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=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>[OH:14][CH2:13][CH2:12][CH2:11][NH:10][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=1[O-:9]

Participants

6

Reactant 4

HCID 64052-Methyl-2-butanolHCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 124874842-Chloro-4-methylpyridine 1-oxide

Product 1

HCID 178428733HCID 178428733, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-methylpyridine-N-oxide (12.1 g, 0.068 mole) (Brown, E. V. J. Amer. Chem. Soc. 1957, 79, 3565), 3-amino-1-propanol (10.33 mL, 0.14 mole), NaHCO3 (28 g, 0.34 mole), and tert-amyl alcohol (70 mL) was heated to reflux. After 16 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. Recrystallization from CH2Cl2/Et2O gave the title compound (10.87 g, 88%) as a yellow solid: TLC (15% MeOH/CH2Cl2) Rf 0.44; 1H NMR (400, CDCl3) δ 7.92 (d, J=6.7, 1 H), 7.28 (br t, 1 H), 6.43 (s, 1 H), 6.33 (dd, J=6.6, 2.1 Hz, 1 H), 3.73 (t, J=5.7 Hz, 2 H), 3.47 (q, H=6.3 Hz, 2 H), 2.29 (s, 3 H), 1.82-1.88 (m, 2 H); MS (ES) m/e 183 (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
  7. customRecrystallization from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-6e05fcffcb8e473da8dfd101419c919c
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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