HCID 15044004, compound → 1,3-Acridinediol, 9-amino-1,2,3,4-tetrahydro-

HRID 248330Notes

Reaction equation

HRID 248330 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]=2

Participants

4

Reactant 1

HCID 15044004HCID 15044004, compound

Product 1

HCID 30728331,3-Acridinediol, 9-amino-1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 23664628LithiumtriethylborohydrideSolvent

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.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. customchromatographed on silica gel (1:2:17-dichloromethane:triethylamine)
  3. customThe appropriate fractions were collected
  4. customEvaporation of the more polar fractions

Sources & evidence

ORD record
ord-911f060cd9f84b57bc6d0a90e8fb5846
Source dataset
uspto-grants-1993_05
Patent number
US05210087

Reaction notes

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