HCID 13935130, compound → 104628-28-6

HRID 580732Notes

Reaction equation

HRID 580732 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9]2[C:10]3[C:15]([N:16]=[C:17]4[C:22]=2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:10]3[C:15]([N:16]=[C:17]4[C:22]=2[CH:21]([OH:23])[CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 13935130HCID 13935130, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025618104628-28-6

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-9-(4-methoxybenzylamino)acridin-1(2H)-one (4.25 g) was dissolved in 75 ml of dry THF and chilled with ice-water. 1M lithium aluminum hydride in THF (7.0 ml) was then added dropwise. After 15 minutes the reaction was quenched by the sequential dropwise addition of 0.4 ml of water, 0.4 ml of 15% sodium hydride and 1.2 ml of water. The inorganic salts were filtered off, the solvents were evaporated, and the residue recrystallized from dichloromethane-ether to give 3.0 g of analytically pure product, mp 163°-165° C.

Workup

  1. customAfter 15 minutes the reaction was quenched by the sequential dropwise addition of 0.4 ml of water, 0.4 ml of 15% sodium hydride and 1.2 ml of water
  2. filtrationThe inorganic salts were filtered off
  3. customthe solvents were evaporated
  4. customthe residue recrystallized from dichloromethane-ether
  5. customto give 3.0 g of analytically pure product, mp 163°-165° C.

Sources & evidence

ORD record
ord-20893bc9e9654c5caddd4d8d0fb575f7
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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