HCID 13935129, compound → 104628-27-5

HRID 1763039Notes

Reaction equation

HRID 1763039 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][C:8]1[C:9]2[C:14]([N:15]=[C:16]3[C:21]=1[C:20](=[O:22])[CH2:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=[CH:11][CH:10]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][C:8]1[C:9]2[C:14]([N:15]=[C:16]3[C:21]=1[CH:20]([OH:22])[CH2:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 13935129HCID 13935129, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3025617104628-27-5

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dihydro-9-(3-methoxybenzylamino)acridin-1(2H)-one (4.0 g) was dissolved in 75 ml of dry THF, the solution was chilled with ice-water, and 1M lithium aluminum hydride (6.5 ml) was added dropwise through a syringe. After 30 minutes TLC showed that the reaction was complete, so the reaction was quenched by the successive 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 the organic phase was evaporated to an oil. Trituration with ether gave a solid that was filtered off and then recrystallizated from ether-pentane to give 2.2 g of analytically pure product, mp 123°-125° C.

Workup

  1. additionwas added dropwise through a syringe
  2. customwas quenched by the successive addition of 0.4 ml of water, 0.4 ml of 15% sodium hydroxide, and 1.2 ml of water
  3. filtrationThe inorganic salts were filtered off
  4. customthe organic phase was evaporated to an oil
  5. customTrituration with ether gave a solid
  6. filtrationthat was filtered off
  7. customto give 2.2 g of analytically pure product, mp 123°-125° C.

Sources & evidence

ORD record
ord-fae5efe48ce2465faf1111c2ad99a582
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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