HCID 14253836, compound → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

HRID 1904727Notes

Reaction equation

HRID 1904727 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[C:18](=[O:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[CH:18]([OH:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 14253836HCID 14253836, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 30256131-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-9-(2-methylbenzylamino)acridin-1(2H)-one (4.15 g) was suspended in 100 ml of THF and chilled with ice-water. 1M lithium aluminum hydride in THF (8.0 ml) was added dropwise through a syringe and then the reaction mixture was stirred 30 minutes in the cold. It 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 and the organic phase was evaporated to obtain an amorphous solid product. Recrystallization from ethyl acetate give 3.38 g, mp 167°-169° C.

Workup

  1. customIt 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
  3. customthe organic phase was evaporated
  4. customto obtain an amorphous solid product
  5. customRecrystallization from ethyl acetate
  6. customgive 3.38 g, mp 167°-169° C.

Sources & evidence

ORD record
ord-5fd661b6c60d4aa0b048e7ba2c787d8e
Source dataset
uspto-grants-1989_06
Patent number
US04839364

Reaction notes

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