Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(methylamino)-

HRID 2309434Notes

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-]>O1CCCC1.CCOCC.[OH-].[K+]>[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 50 ml 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 32 ml (1 eq) of 1.1M 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 1 ml of saturated NH4Cl and the resulting salts dissolved in 30% potassium hydroxide solution. The tetrahydrofuran solution was separated and evaporated to an oil which solidified upon trituration with 1:1 dichloromethane/hexanes. The solid was recrystallized from 10:1 hexanes/tetrahydrofuran to yield 5.89 g (73%) of a solid, melting point 160°-161° C. ANALYSIS: Calculated for C14H16N2O: 73.65% C, 7.06% H, 12.27% N. Found: 73.61% C, 7.00% H, 12.39% N.

Workup

additionafter the addition
customThe tetrahydrofuran solution was separated
customevaporated to an oil which
customThe solid was recrystallized from 10:1 hexanes/tetrahydrofuran

Sources & evidence

ORD record: ord-95d29627a5a7493a9eaf17d3c97a735b
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695573

Reaction notes

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