N,N-Diethylaniline → 2-Hydroxy-1-naphthamide

HRID 393572

Reaktionsgleichung

Reaktionsgleichung von HRID 393572
CC[N:3](C1C=CC=CC=1)CC.[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[C:23]([OH:25])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1>[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[C:23]([NH2:3])=[O:25]

Komponenten

6

Edukt 4

HCID 7061N,N-DiethylanilineHCID 167902-Hydroxy-1-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 151052242-Hydroxy-1-naphthamideAusbeute 345,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Diethylaniline (0.27 μL, 1.7 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (0.8 mg, 1.5 μmol, 1 equiv) in THF (0.2 mL) at 0° C. under an argon atmosphere and the solution was stirred for 5 min. 2-Hydroxy-1-naphthoic acid (0.37 mg, 2.0 μmol, 1.3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.38 mg, 2.0 μmol, 1.3 equiv) and 1-hydroxybenzotriazole (0.25 mg, 1.8 μmol, 1.2 equiv) were then added separately, each in one portion, to the above solution at 0° C. The reaction mixture was warmed to 23° C. over 13 h 20 min, then was quenched with saturated aqueous ammonium chloride solution (3 mL). The mixture was diluted with ethyl acetate (10 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layer was dried over sodium sulfate. Concentration in vacuo left a white solid, which was purified by flash column chromatography (85% ethyl acetate-hexanes) to give the 2-hydroxy-naphthalene-1-carboxylic acid amide derivative (1.1 mg, 100%) as a white solid.

Aufarbeitung

  1. customat 0° C
  2. customwas quenched with saturated aqueous ammonium chloride solution (3 mL)
  3. additionThe mixture was diluted with ethyl acetate (10 mL)
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
  6. dry with materialthe combined organic layer was dried over sodium sulfate
  7. concentrationConcentration in vacuo
  8. waitleft a white solid, which
  9. customwas purified by flash column chromatography (85% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3b78a769ebff43a498e45b363e11f4fc
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809099B2

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