Hydrochloric Acid → 9-Amino-1,2,3,4-tetrahydroacridine hydrate

反応式

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.Cl>>[OH2:16].[NH2:5][C:4]1[C:3]2[C:2]([N:1]=[C:10]3[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

反応物 3

HCID 313Hydrochloric Acid2 回

HCID 7967Cyclohexanone

HCID 729132-Aminobenzonitrile

生成物 1

HCID 197952369-Amino-1,2,3,4-tetrahydroacridine hydrate収率 67%

実験手順

A mixture of 2-aminobenzonitrile (120 g), cyclohexanone (115.8 ml), conc hydrochloric acid (9.2 ml), and cuprous chloride (1.21 g) was heated under reflux for 3 days, with stirring. At the end of each 24 hr period, additional cuprous chloride (1.21 g) was added. At the end of the 3rd day, additional conc hydrochloric acid (47.3 ml) was added, and the mixture was cooled to ambient temperature. The precipitate was collected and washed with 10% hydrochloric acid to provide 160 g (67.0%) of 9-amino-1,2,3,4-tetrahydroacridine hydrate, mp 180°-185°.