HCID 13935157, compound → HCID 13935153, compound

HRID 580724Notes

Reaction equation

HRID 580724 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[C:21](=[O:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][C:13]([CH3:24])=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]([OH:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][C:13]([CH3:24])=[CH:12][CH:11]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13935157HCID 13935157, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13935153HCID 13935153, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of 3.6 g of 9-benzylamino-3,4-dihydro-6-methylacridin-1(2H)-one in 80 ml of tetrahydrofuran was added 6 ml of 1M solution of lithium aluminum hydride in THF. This was stirred for 1 hour, and thereafter quenched with 7 ml of saturated ammonium chloride solution. The inorganics were filtered and rinsed with ethyl acetate and the combined organics were dried over anhydrous magnesium sulfate. The resulting solid was triturated with ethyl ether to obtain 3.15 g of a solid, mp 148°-153° C. This was recrystallized from toulene (70 ml) to obtain 2.5 g of an analytically pure solid, mp 149°-152° C.

Workup

  1. customquenched with 7 ml of saturated ammonium chloride solution
  2. filtrationThe inorganics were filtered
  3. washrinsed with ethyl acetate
  4. dry with materialthe combined organics were dried over anhydrous magnesium sulfate
  5. customThe resulting solid was triturated with ethyl ether

Sources & evidence

ORD record
ord-c0ce646f29f143b3ad45ac11718a997e
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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