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

반응식

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

참가 물질

실험 절차

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.