Acetic Acid → 2-(2', 4'-Dioxo-1'-methyl-cyclohexyl)-benzyl amine

反応式

C1CO[CH:8]2[CH:3]([CH2:4][C:5](=[O:24])[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18]C(N=[N+]=[N-])=O)([CH3:11])[CH2:7]2)[O:2]1.C(O)(=O)C.C[N:30](C)C=O>>[O:24]=[C:5]1[CH2:4][C:3](=[O:2])[CH2:8][CH2:7][C:6]1([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH2:30])[CH3:11]

参加物

反応物 3

HCID 176Acetic Acid

HCID 6228Dimethylformamide

HCID 867507072-(4'-Ethylenedioxy-1'-methyl-2'-oxocyclohexyl)-phenylacetyl azide

生成物 1

HCID 677265002-(2', 4'-Dioxo-1'-methyl-cyclohexyl)-benzyl amine

反応条件

温度: 100 °C

実験手順

The acyl azide 5 is dissolved in dimethylformamide and heated to 100° C. until nitrogen evolution ceases. The solution is cooled and treated with aqueous acetic acid to form 2-(2', 4'-dioxo-1'-methyl-cyclohexyl)-benzyl amine 6. Diethyl ether is added and the solution is washed successively with saturated sodium bicarbonate solution, water, and saturated salt solution and dried over anhydrous sodium sulfate. The solvent is removed by rotoevaporation to yield 1,2,3,4,4a,5,6,10b-octahydro- 10b-methyl-3-phenanthridinone 7.

後処理

temperatureThe solution is cooled

出典と根拠

ORDレコード: ord-93a7c98bbcbc472580c091492ec5d4fa
出典データセット: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05621104

反応ノート

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