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

HRID 1769645Notes

Reaction equation

HRID 1769645 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-7df3e973ebee4f888c4d1d5fbbb64f47
Source dataset
uspto-grants-1995_01
Patent number
US05382594

Reaction notes

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