HCID 13935126, compound → 104628-25-3

HRID 2309467Notes

Reaction equation

HRID 2309467 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]2[C:9]3[C:14]([N:15]=[C:16]4[C:21]=2[C:20](=[O:22])[CH2:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[C:9]3[C:14]([N:15]=[C:16]4[C:21]=2[CH:20]([OH:22])[CH2:19][CH2:18][CH2:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 13935126HCID 13935126, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025615104628-25-3

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-9-(4-methylbenzylamino)acridin-1(2H)-one (5.71 g) was dissolved in 100 ml of dry THF, chilled with ice-water, and then 9.0 ml of 1M lithium aluminum hydride in THF was added. After 15 minutes the reaction was quenched by the sequential addition of 0.4 ml of water, 0.4 ml of 15% sodium hydroxide, and 1.2 ml of water. The inorganic salts were filtered off and washed with warm THF and then the combined organic phase was evaporated and the residue recrystallized from dichloromethane-pentane to obtain 4.77 g of analytically pure product, mp 176°-178° C.

Workup

  1. customAfter 15 minutes the reaction was quenched by the sequential addition of 0.4 ml of water, 0.4 ml of 15% sodium hydroxide, and 1.2 ml of water
  2. filtrationThe inorganic salts were filtered off
  3. washwashed with warm THF
  4. customthe combined organic phase was evaporated
  5. customthe residue recrystallized from dichloromethane-pentane
  6. customto obtain 4.77 g of analytically pure product, mp 176°-178° C.

Sources & evidence

ORD record
ord-35635233c0da46edba5deb5cbbb4c257
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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