Potassium Hydroxide → Velnacrine

HRID 1249402Notes

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 100 ml 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 21.4 ml (1.0 eq) of 1.1M 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 2 ml of saturated NH4Cl and the salts were dissolved with 30% potassium hydroxide. The insoluble product was filtered off and rinsed with water. The precipitate 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 precipitate 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-d9b589e6246141b3baba35dd48aa0134
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04631286

Reaction notes

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