HCID 13935133, compound → 104628-31-1

HRID 1904733Notes

Reaction equation

HRID 1904733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][C:10]1=[O:25])=[N:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH:10]1[OH:25])=[N:5]2

Participants

4

Reactant 2

HCID 13935133HCID 13935133, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025621104628-31-1Yield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

In 100 ml of dry THF was added 4.06 g of 6-chloro-3,4-dihydro-9-(4-fluorobenzylamino)acridin-1(2H)-one and the mechanically stirred solution was cooled to 10° C. under a nitrogen atmosphere. To the reaction was added 5.8 ml of 1M LiAlH4 in THF over 15 minutes. After 1/2 hour the reaction was complete by TLC analysis, so it was quenched with 1 ml of saturated ammonium chloride solution and the inorganic salts were filtered off. The filtrate was evaporated to a solid which was recrystallized from dichloromethane to yield 3.18 g of solid. The compound went through a crystal structure change at 176°-177° C. before melting at 187°-188° C.

Workup

  1. customwas quenched with 1 ml of saturated ammonium chloride solution
  2. filtrationthe inorganic salts were filtered off
  3. customThe filtrate was evaporated to a solid which
  4. customwas recrystallized from dichloromethane

Sources & evidence

ORD record
ord-6164a18d4fa944319163b523e687459d
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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