Potassium Cyanide → HCID 54082021, compound

HRID 1941069Notes

Reaction equation

HRID 1941069 reaction equation
Cl[C:2]1[C:3]2[CH:4]=[C:5]([O:20][CH3:21])[CH:6]=[CH:7][C:8]=2[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=[CH:11]2.[C-]#N.[K+].[Cu][C:26]#[N:27]>CO>[C:26]([C:2]1[C:3]2[CH:4]=[C:5]([O:20][CH3:21])[CH:6]=[CH:7][C:8]=2[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=[CH:11]2)#[N:27]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 54401656HCID 54401656, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 54082021HCID 54082021, compoundYield 176%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 12-chloro-2-methoxy-benz[b]acridine (562 mg, 1.905 mmol), potassium cyanide (136 mg, 2.096 mmol) and copper(I) cyanide (86 mg, 0.953 mmol) in methanol. (3.7 ml) was stirred at 170° C. in a sealed-tube for 4.5 hours. The resulting mixture was filtrated, and the solid was washed with chloroform/methanol (2:1, 10 ml). The combined filtrate was evaporated under reduced pressure to give a residue, which was flash-chromatographed on a silica column packed with chloroform and eluted with 1% methanol/chloroform to yield 12-cyano-2-methoxy-benz[b]acridine (477 mg, 88%). Rf 0.6 (silica gel, 1% methanol/chloroform). MS (CI, CH4): m/z 285 (M+1).

Workup

  1. filtrationThe resulting mixture was filtrated
  2. washthe solid was washed with chloroform/methanol (2:1, 10 ml)
  3. customThe combined filtrate was evaporated under reduced pressure
  4. customto give a residue, which
  5. customwas flash-chromatographed on a silica column
  6. washeluted with 1% methanol/chloroform

Sources & evidence

ORD record
ord-6536444ba79a49d89c2c1662c9149fd4
Source dataset
uspto-grants-1997_12
Patent number
US05702887

Reaction notes

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