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

HRID 1441117Notes

Reaction equation

HRID 1441117 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-I (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-amino1,2,3,4-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-60ddab92f33947a5be8c264534dbf883
Source dataset
uspto-grants-1996_03
Patent number
US05502203

Reaction notes

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