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

HRID 580698Notes

Reaction equation

HRID 580698 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

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 13756050HCID 13756050, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 30256321-Acridinol, 1,2,3,4-tetrahydro-9-(methylamino)-Yield 73%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-173363e6092d4e09b0e26a35a3bc4aaa
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

Loading…