Potassium Hydroxide → Velnacrine

HRID 1763005Notes

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][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].[OH-].[K+]>O1CCCC1.CCOCC>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

Conditions

Temperature: -5 °C

Procedure

In 100ml of dry tetrahydrofuran was added 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one. The mechanically stirred suspension was cooled to -5° C. and 21.4ml (1.0 eq) of 1.1 M LiAlH4 solution in ether was added dropwise. After completion of the addition, the reaction mixture was stirred further for 2 hours, whereupon the reaction appeared complete based on thin layer chromatography analysis. The LiAlH4 was neutralized with 2ml of saturated NH4Cl and the salts were dissolved with 30% potassium hydroxide. The insoluble product was filtered off and rinsed with water. The procipitate was then dissolved in 3N HCl and the residual insoluble salts filtered off. The acid solution was washed with EtOAc and made basic (pH 9) with 10% NaOH. The precipitated product was filtered and washed with water. After drying at 80° C. under vacuum overnight, 4.15 g (82%) of a powder was obtained, melting point 245° C.

Workup

additionAfter completion of the addition
filtrationThe insoluble product was filtered off
washrinsed with water
dissolutionThe procipitate was then dissolved in 3N HCl
filtrationthe residual insoluble salts filtered off
washThe acid solution was washed with EtOAc
filtrationThe precipitated product was filtered
washwashed with water
customAfter drying at 80° C. under vacuum overnight

Sources & evidence

ORD record: ord-6f0529058c64400e86c9e68811355a3c
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835275

Reaction notes

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