HCID 13935125, compound → 104628-24-2

HRID 2309466Notes

Reaction equation

HRID 2309466 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 13935125HCID 13935125, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025614104628-24-2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-9-(3-methylbenzylamino)acridin-1(2H)-one (3.70 g) was dissolved in 100 ml of dry THF and chilled in ice-water. 1M lithium aluminum hydride in THF (7.0 ml) was added and the reaction stirred 30 minutes in the cold. The reaction mixture was quenched by the sequential addition of 0.5 ml of water, 0.5 ml of 15% sodium hydroxide and 1.5 ml of water. The inorganic salts were filtered from the reaction mixture and the organic phase was evaporated to an oil. Trituration with ether gave a solid that was recrystallized from ethyl acetate/pentane to obtain 3.22 g, mp 133°-134° C.

Workup

  1. customThe reaction mixture was quenched by the sequential addition of 0.5 ml of water, 0.5 ml of 15% sodium hydroxide and 1.5 ml of water
  2. filtrationThe inorganic salts were filtered from the reaction mixture
  3. customthe organic phase was evaporated to an oil
  4. customTrituration with ether gave a solid
  5. customthat was recrystallized from ethyl acetate/pentane
  6. customto obtain 3.22 g, mp 133°-134° C.

Sources & evidence

ORD record
ord-3783b16b70804d378af5aee625ca29fc
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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