Potassium Cyanide → HCID 14853009, compound

HRID 845060Notes

Reaction equation

HRID 845060 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]2.N([O-])=O.[Na+].[C-:17]#[N:18].[K+]>F[B-](F)(F)F.[H+].O>[C:17]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]2)#[N:18]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 20133471HCID 20133471, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14853009HCID 14853009, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 28118Tetrafluoroboric acidSolvent

Procedure

A solution of 5-amino-2-methyl-1-indanone (10.0 g) in fluoroboric acid (40%;28.0 ml ) was treated at 0°-5° with sodium nitrite (4.7 g) in water (8.0 ml ). The diazonium salt solution was added to cuprous cyanide (25.0 g) in potassium cyanide (37.5 g) in water (100 ml ) at 40°. The mixture was stirred at 10° for 10 minutes, cooled and extracted with chloroform. The extract was evaporated and the residue recrystallised from aqueous ethanol to give 5-cyano-2-methyl-1-indanone(7.89 g; m.p. 90°-1°) which was converted into 7-cyano-4,4a-dihydro-[5H]-indeno[1,2-c]pyridazin-3[2H]-one by the procedures given in method A (iii, iv).

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. customThe extract was evaporated
  4. customthe residue recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-3d31b34163494980864f4c15fa631fc4
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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