Ethanol → HCID 19958919, compound

HRID 54450Notes

Reaction equation

HRID 54450 reaction equation
[C:1]1([CH:7]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:14][C:13]3[CH2:12][CH2:11][CH2:10][C:9](=O)[C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)C>N1C=CC=CC=1>[C:1]1([CH:7]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:14][C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7966959-Phenyl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dioneHCID 4311764Sodium borohydride

Product 1

HCID 19958919HCID 19958919, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 9-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (5.0 g), sodium borohydride (6.5 g), ethanol (150 mL) and pyridine (50 mL) was heated at 70° C. overnight and cooled to room temperature. The solvent was removed, the residue partitioned between water and ethyl acetate, the organic layer was dried and the solvent removed. Chromatography (methylene chloride/methanol; 98/2) provided the title compound (3.0g) as a white solid. Recrystallization from ethanol/hexane returned analytically pure title compound, mp 252°-254° C., NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.03-2.13 (m,4, CH2), 2.38-2.44 (m,2, CH2), 4.14 (s,1, CH), 7.04-7.21 (m,5, Ar) 8.34 (s,1, NH); (CI, CH4) MS: m/z=280(M+1). Analysis for C19H21NO.0.2H2O: Calculated: C, 80.64; H, 7.62; N, 4.95; Found: C, 80.84; H, 7.62; N, 4.80.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed
  3. customthe residue partitioned between water and ethyl acetate
  4. customthe organic layer was dried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-2a10923609c94fc8871bdc71619674a6
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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