9-amino-3,4-dihydroacridin-1(2H)-one → HCID 13756059, compound

HRID 2309438Notes

Reaction equation

HRID 2309438 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:17][Li]>O1CCCC1.CCOCC>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]([CH3:17])([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 2

HCID 1843619-amino-3,4-dihydroacridin-1(2H)-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 13756059HCID 13756059, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of dry tetrahydrofuran was suspended 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one at ice temperature and 78 ml (4 eq) of 1.2M CH3Li solution in ether was added thereto at such a rate as to avoid bubbling. The reaction mixture was stirred overnight as it warmed to ambient temperature. The next day 20 ml more of the CH3Li solution was added to drive the reaction to a completion. After 0.5 hour the reaction was quenched with excess water and 4.97 g of the precipitate was collected and air dried. The product was recrystallized from MeOH/toluene. The yield was 2.06 g (38%) of granules, melting point 250° C.

Workup

  1. additionwas added
  2. customat such a rate as to avoid bubbling
  3. additionThe next day 20 ml more of the CH3Li solution was added
  4. customthe reaction to a completion
  5. customAfter 0.5 hour the reaction was quenched with excess water and 4.97 g of the precipitate
  6. customwas collected
  7. customair dried
  8. customThe product was recrystallized from MeOH/toluene

Sources & evidence

ORD record
ord-8ecd090c7b5b49c18c0d804bab61d67c
Source dataset
uspto-grants-1987_09
Patent number
US04695573

Reaction notes

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