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

HRID 54435Notes

Reaction equation

HRID 54435 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:22]3[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]3[CH2:14][CH2:13][CH2:12][C:11](=O)[C:10]2=3)[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+].C(O)C.O>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:22]3[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=3)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 98400009-(3-cyanophenyl)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione

Product 1

HCID 193812379-(3-Cyanophenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridineone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 9-(3-cyanophenyl)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione (3.18 g), sodium borohydride (2.50 g) and 50 mL of ethanol was stirred at 70° C. overnight. The mixture was treated with about 300 mL of water, stirred for several hours and the solid collected by suction filtration, slurried on the funnel with a little ethanol and sucked dry on the funnel. The solid (1.87 g) was combined with 0.49 g of material from a previous run and the combined material was chromatographed, with methanol:dichloromethane (2.5:97.5) as elutent. The solvent evaporated and the residue taken up in 50 mL of methanol and about 20 mL of methylene chloride. The solution was concentrated on a steam bath until crystals started to form, was treated with an equal volume of ethyl acetate and refrigerated overnight. The title compound was obtained as bright yellow crystals (1.16 g); mp 246°-249° C.; NMR: 1.47 (broad s,2, CH2), 1.65-1.87 (m,6, CH2), 2.11 (m,4, CH2), 2.39-2.51 (m,2, CH2), 4.25 (s,1, CH), 7.41-7.57 (m,4, Ar), 8.45 (s,1, NH); (CI, CH4) MS: m/z=305(M+1). Analysis for C20H20N2O: Calculated: C, 78.92; H, 6.62; N, 9.20; Found: C, 78.64; H, 6.65; N, 9.08.

Workup

  1. stirringstirred for several hours
  2. filtrationthe solid collected by suction filtration
  3. customsucked dry on the funnel
  4. customthe combined material was chromatographed, with methanol:dichloromethane (2.5:97.5) as elutent
  5. customThe solvent evaporated
  6. concentrationThe solution was concentrated on a steam bath until crystals
  7. customto form

Sources & evidence

ORD record
ord-0733fd102a8041368bb4c44f09ec4807
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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