Water → 4-(2,2,2-Trimethylacetamido)pyridine

HRID 268592

Reaktionsgleichung

Reaktionsgleichung von HRID 268592
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 17274-AminopyridineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Produkt 1

HCID 4270594-(2,2,2-Trimethylacetamido)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Following procedures generally taught in J. A. Turner, J. Org. Chem. 1983, 48, 3401-3408, a solution of pivaloyl chloride (13.5 mL, 110 mmol) in CH2Cl2 (20 mL) was slowly added to an ice-cold solution of 4-aminopyridine (9.41 g, 100 mmol) and triethylamine (17.4 mL, 125 mmol) in CH2Cl2 (150 mL). After addition was complete, the resulting mixture was warmed to room temperature and stirred for 2 h. The solution was poured into water, the CH2Cl2 layer was washed with dilute NaHCO3, dried over Na2SO4, and evaporated to leave a light brown solid. Recrystallization from EtOAc/hexanes afforded the product as a white crystal, which was collected by vacuum filtration (13.03 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=4.8 Hz, 2 H), 7.50 (d, J=4.8 Hz, 2 H), 7.44 (br s, 1 H), 1.33 (s, 9 H). MS (LR-APCI) calcd. for C10H15N2O (M+H) 179.1; found 179.1.

Aufarbeitung

  1. additionAfter addition
  2. washthe CH2Cl2 layer was washed with dilute NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto leave a light brown solid
  6. customRecrystallization from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-730f9b9421974f4a811c48bbfe888c08
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446112B2

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