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

HRID 54449Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[BH4-].[Na+].C(O)C>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 9-(3-fluorophenyl)-3,4, 6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (5.0 g), sodium borohydride (6.1 g), ethanol (140 mL) and pyridine (50 mL) was heated at 70° C. overnight and cooled to room temperature. The solvent was removed and the resulting yellow solid was collected and washed well with water. Chromatography (ethyl acetate/hexane; 80/20) provided the title compound (2.1 g) as a yellow solid. Recrystallization from ethanol/hexane returned analytically pure light yellow solid, mp 249°-251° C.; NMR: 1.45-1.55 (m,3, CH2), 1.66-1.90 (m,5, CH2); 2.10-2.15 (m,4, CH2), 2.39-2.45 (m,2, CH2 (s,1, CH), 6.87-6.92 (m,2, Ar), 7.00 (d,1, J=7.8, Ar), 7.20-7.27 (m,1, Ar), 8.41 (s,1, NH); (CI, CH4) MS: m/z=298(M+1). Analysis for C19H20FNO: Calculated: C, 76.74; H, 6.78; N, 4.71; Found: C, 76.32; H, 6.71; N, 4.62.

Workup

temperaturecooled to room temperature
customThe solvent was removed
customthe resulting yellow solid was collected
washwashed well with water

Sources & evidence

ORD record: ord-655f7975c96b4cadb314cb9a43ca0ef7
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622964

Reaction notes

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