4-Methoxybenzylamine → HCID 23856703, Verbindung

HRID 901236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901236
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Cl[C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:12]2[N:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 762582-Chloronicotinic acid

Produkt 1

HCID 23856703HCID 23856703, VerbindungAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

p-Methoxybenzylamine (8.24 mL, 63.5 mmol) was added to a solution of 2-chloronicotinic acid (5 g, 31.7 mmol) in pyridine and refluxed overnight. The pyridine was distilled and the residue was dissolved in 1N NaOH. The solution was diluted with water to adjust the pH to 10 to 11 and washed by dichloromethane. The aqueous phase was neutralized with cold aqueous 10% HCl solution to adjust the pH to 4 to 5. The solids formed were filtered, washed with cold water, and dried in a vacuum oven to yield 6.32 g (77%) of 2-(4-methoxy-benzylamino)-nicotinic acid (11) as white solids. MP: 229° C.; 1H-NMR (DMSO-d6): δ 3.72 (s, 3H), 4.60 (d, J=3.6 Hz, 2H), 6.40 (dd, J=4.9, 7.7 Hz, 1H), 6.62 (d, J=7.6 Hz, 2H), 7.25 (d, J=7.6 Hz, 2H), 8.09 (dd, J=1.8, 7.0 Hz, 1H), 8.26 (dd, J=1.8, 7.0 Hz, 1H), 8.48 (br. s, 1H), 13.11 (s, 1H); EIMS: 259 (M+1), 281 (M+23).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. distillationThe pyridine was distilled
  3. dissolutionthe residue was dissolved in 1N NaOH
  4. additionThe solution was diluted with water
  5. washwashed by dichloromethane
  6. customThe solids formed
  7. filtrationwere filtered
  8. washwashed with cold water
  9. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-f395fbfa563143b4be4d79e1b0baa0e0
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361760B2

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