1-Naphthalenemethanamine → N-(1-Naphthylmethyl)-chroman-2-carboxamide

HRID 129579

Reaktionsgleichung

Reaktionsgleichung von HRID 129579
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([O:15]CC)=O)[CH2:9][CH2:8]2.[NH2:18][CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[C-]#N.[K+]>C1(C)C=CC=CC=1>[C:20]1([CH2:19][NH:18][C:13]([CH:10]2[CH2:9][CH2:8][C:7]3[C:12](=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:11]2)=[O:15])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 83551-NaphthalenemethanamineHCID 9032Potassium CyanideHCID 18787171Ethyl 8-methoxy-chroman-2-carboxylate

Produkt 1

HCID 21843746N-(1-Naphthylmethyl)-chroman-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

33.0 g (0.14 mol) of ethyl 8-methoxy-chroman-2-carboxylate (content 87%) are heated together with 25.8 g (0.16 mol) of 1-aminomethylnaphthalene and 0.05 g of potassium cyanide at 120° C. for 8 hours and then at 130° C. for 2 hours. After cooling, the mixture is diluted with 100 ml of toluene and this solution is introduced onto silica gel K60. Elution with cyclohexane/ethyl acetate mixtures (100:0to 75:25) gives the amide in the form of a viscous syrup (32.9 g, 68%), which can be further reacted directly.

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthis solution is introduced onto silica gel K60
  3. washElution with cyclohexane/ethyl acetate mixtures (100:0to 75:25)

Quellen und Nachweise

ORD-Eintrag
ord-67b2a613d3b44b75b2c7b5be93d5a2f1
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468882

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