Potassium Hydroxide → 1-Acridinol, 1,2,3,4-tetrahydro-9-(methylamino)-

HRID 1763007Notes

Reaction equation

[CH3:1][NH:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].[OH-].[K+]>O1CCCC1.CCOCC>[CH3:1][NH:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH:15]([OH:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

Conditions

Temperature: -10 °C

Procedure

In 50ml of dry tetrahydrofuran was dissolved 8.00 g of 3,4-dihydro-9-(methylamino)acridin-1(2H)-one. The mechanically stirred solution was cooled to -10° C. under N2 and 32ml (1 eq) of 1.1 M LiAlH4 solution in ether was added over 5 minutes. The stirring was continued for 45 minutes after the addition, during which the reaction went to completion. The excess LiAlH4 was neutralized with 1ml of saturated NH4Cl and the resulting salts dissolved in - 30% potassium hydroxide solution. The tetra-hydrofuran solution was separated and evaporated to an oil which solidified upon trituration with 1:1 dichloromethane/hexanes.

Workup

additionafter the addition
customThe tetra-hydrofuran solution was separated
customevaporated to an oil which

Sources & evidence

ORD record: ord-c815279698924bc2b9ec4e4d35a51875
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835275

Reaction notes

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