p-Toluenesulfonic acid → 1-{6-[(1E)-N-(2,6-Dimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

HRID 707726

Reaktionsgleichung

Reaktionsgleichung von HRID 707726
[C:1]([C:4]1[N:9]=[C:8]([C:10](=O)[CH3:11])[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[NH2:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CC>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[N:21]=[C:10]([C:8]1[N:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][CH:7]=1)[CH3:11]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 68962,6-DimethylanilineHCID 707902,6-Diacetylpyridine

Produkt 1

HCID 220656241-{6-[(1E)-N-(2,6-Dimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

1-(6-Acetyl-pyridin-2-yl)-ethanone 2 (22.2 g, 0.0136 mole), 15.0 g (0.124 mol) of 2,6-dimethyl-phenylamine 3, 300 ml of n-propanol, and a few crystals of p-toluenesulfonic acid were stirred at room temperature for 36 h in 500 ml flask under a flow of nitrogen. The resultant yellow precipitate was filtered and washed by 20 ml of methanol. It was then dried at 1-mm vacuum overnight. The yield of 1-{6-[1-(2,6-dimethyl-phenylimino)-ethyl]-pyridin-2-yl}-ethanone 1 was 12.86 g (39%) as a yellow solid. 1H NMR (500 MHz, CD2Cl2, TMS): δ 2.00 (s, 6H, Me), 2.20 (s, 3H, Me), 2.70 (s, 3H, Me), 6.90 (t, 3JHH=8.1 Hz, 1H, Arom-H), 7.10 (d, 3JHH=8.1 Hz, 2H, Arom-H), 7.95 (t, 3JHH=8.0 Hz, 1H, Pyr-H), 8.10 (d, 3JHH=8.0 Hz, 1H, Py-H), 8.55 (d, 3JHH=8.0 Hz, 1H, Py-H). 13C NMR (500 MHz, CD2Cl2, TMS (selected signals)): δ 167.1 (C═N), 200.1 (0=0). Anal. Calculated for C17H13N2O (Mol. Wt.: 266.34): C, 76.66; H, 6.81; N, 10.52. Found: C, 76.69; H, 6.84; N, 10.57.

Aufarbeitung

  1. filtrationThe resultant yellow precipitate was filtered
  2. washwashed by 20 ml of methanol
  3. dry with materialIt was then dried at 1-mm vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-337142eca1f542c9ab4de866ed5bfdac
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175104B2

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