HCID 13935127, compound → 9-[(2-methoxyphenyl)methylamino]-1,2,3,4-tetrahydroacridin-1-ol

HRID 1763038Notes

Reaction equation

HRID 1763038 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=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][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=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 13935127HCID 13935127, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 30256169-[(2-methoxyphenyl)methylamino]-1,2,3,4-tetrahydroacridin-1-olYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,4-Dihydro-9-(2-methoxybenzylamino)acridin-1(2H)-one (4.0 g) was dissolved in 100 ml of dry THF and chilled in ice-water. 1M lithium aluminum hydride in THF (6.5 ml) was added through a syringe. The reaction mixture was stirred 30 minutes in the cold and then an additional 2.0 ml of 1M lithium aluminum hydride solution was added. 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 and the organic phase was evaporated to a gum. Trituration with ether gave a solid (2.95 g). Analytically pure material was obtained by recrystallization from ethyl acetate-pentate, mp 115°-117° C.

Workup

  1. additionwas added
  2. 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
  3. filtrationThe inorganic salts were filtered from the reaction
  4. customthe organic phase was evaporated to a gum

Sources & evidence

ORD record
ord-d9541c710d9c4987a40fa2189c9bffb3
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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