HCID 15044004, compound → 1,3-Acridinediol, 9-amino-1,2,3,4-tetrahydro-
Reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH:12]([OH:17])[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2>O1CCCC1.C([BH-](CC)CC)C.[Li+]>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH:12]([OH:17])[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 9-amino-3,4-dihydro-3-hydroxyacridin-1 (2H)-one (2.07 g) in tetrahydrofuran (125 ml), lithium triethylborohydride (1 molar in tetrahydrofuran, 27 ml) was allowed to stand for 0.5 hrs. The reaction mixture was quenched with methanol. The mixture was preadsorbed on silica, and flash chromatographed on silica gel (1:2:17-dichloromethane:triethylamine). The appropriate fractions were collected. Evaporation of the more polar fractions gave 0.541 (25.8%) of 9-amino-1,2,3,4-tetrahydro-1,3-acridinediol, mp 139°-141° C.