HCID 13935130, compound → 104628-28-6

HRID 1763040Notes

Reaction equation

HRID 1763040 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 15sodium hydride and 1.2 ml of water. The inorganic salts were filtered off, the solvents were evaporated, and the residue recrystallized from dichloromrthane-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 15sodium hydride and 1.2 ml of water
  2. filtrationThe inorganic salts were filtered off
  3. customthe solvents were evaporated
  4. customthe residue recrystallized from dichloromrthane-ether
  5. customto give 3.0 g of analytically pure product, mp 163°-165° C.

Sources & evidence

ORD record
ord-e0a7289b379d407685e78dd712555b5d
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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