Lithium hydride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

HRID 1763035Notes

Reaction equation

HRID 1763035 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-].[Li+]>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 62714Lithium hydrideHCID 14253836HCID 14253836, compound

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 hydride in THF (8.0 ml) was added dropwise through a syringe and then the reactionh 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 gave 3.38 g, mp 167°-169° C.1

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. customgave 3.38 g, mp 167°-169° C

Sources & evidence

ORD record
ord-ade569a3f0bc4ff995db9bef8dce8b4a
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

Loading…