Diethyl Ether → 10-Methyl-9,10-dihydroacridine-9-carbonitrile

HRID 726766Notes

Reaction equation

HRID 726766 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:15](OCC)C.[C-:20]#[N:21].[K+]>O>[C:20]([CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]([CH3:15])[C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)#[N:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 9215Acridine

Product 1

HCID 1558421810-Methyl-9,10-dihydroacridine-9-carbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 10.0 g (43.5 mmol) of acridine chloromethylate [A. Kaufmann et al, Ber. Dt. Chem. Ges. 42, 1999 (1909)]in 100 ml of water is covered with a layer of 200 ml of diethyl ether, and a solution of 3.13 g (48.0 mmol) of potassium cyanide in 20 ml of water is added. After about 30 minutes, the ether phase is separated off, the mixture is concentrated to 50 ml on a vacuum rotary evaporator and the product which has precipitated is filtered off. Crystallization of the crude product from ethanol gives 7.10 g (75%) of 9-cyano-9,10-dihydro-10-methyl-acridine, melting point 141°-143° C. (compound (106), Table 1).

Workup

  1. customthe ether phase is separated off
  2. concentrationthe mixture is concentrated to 50 ml on a vacuum rotary evaporator
  3. customthe product which has precipitated
  4. filtrationis filtered off
  5. customCrystallization of the crude product from ethanol

Sources & evidence

ORD record
ord-72063272b77248fa85edf094e6661750
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

Loading…