Ethanol → 9-(4-Chlorophenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridinone

HRID 54452Notes

Reaction equation

HRID 54452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:21]3[C:20](=O)[CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][C:14]3[CH2:13][CH2:12][CH2:11][C:10](=[O:23])[C:9]2=3)=[CH:4][CH:3]=1.C(O)C.[BH4-].[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:10](=[O:23])[CH2:11][CH2:12][CH2:13][C:14]=3[NH:15][C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:21]2=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10887399-(4-Chlorophenyl)-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dioneHCID 4311764Sodium borohydride

Product 1

HCID 199588969-(4-Chlorophenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridinoneYield 17.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred 70° C. mixture of 9-(4-chlorophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (6.0 g), ethanol (160 mL) and pyridine (50 mL) was added sodium borohydride (7.5 g, 198.4 mmole) in two portions over six hours. The solvent was removed; the resulting yellow solid washed well with water and dried in vacuo. Chromatography (methylene chloride/ethyl acetate; 85/15) and recrystallization from ethanol provided the title compound (1.0 g) as a white solid, mp 253°-254° C.; NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.07-2.14 (m,4, CH2), 2.38-2.41 (m,2, CH2), 4.16 (s,1, CH), 7.16 (d,2, J=8.4, Ar), 7.25 (d,2, J=8.4, Ar), 8.39 (s,1, NH); (CI, CH4) MS: m/z=314(M+1). Analysis for C19H20ClNO: Calculated: C, 72.72; H, 6.37; N, 4.46; Found: C, 72.35; H, 6.60; N, 4.29.

Workup

  1. customThe solvent was removed
  2. washthe resulting yellow solid washed well with water
  3. customdried in vacuo
  4. customChromatography (methylene chloride/ethyl acetate; 85/15) and recrystallization from ethanol

Sources & evidence

ORD record
ord-9dfea6b2456b4920bd0c99ed3c3fb1ca
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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