Potassium Cyanide → HCID 178510113, compound

HRID 2289939Notes

Reaction equation

HRID 2289939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[C-:25]#[N:26].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:25]#[N:26])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 178522917HCID 178522917, compound

Product 1

HCID 178510113HCID 178510113, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide of Example No. 5 (0.19 g), Pd(PPh3)4 (0.10 g), and KCN (0.06 g) are heated at 60° C. in 60 mL freshly distilled tetrahydrofuran. The reaction is cooled to room temperature. The solid in the reaction mixture is filtered. Thin layer chromatography shows the desired product in the filtrate and the solid. Both are dissolved in a MeOH:CH2Cl2 mixture and adsorbed onto silica. The residue is chromatographed eluting with 3% MeOH:CH2Cl2 (1 L), followed by 4% MeOH:CH2Cl2 (1 L), and 5% MeOH:CH2Cl2 (1 L). The product-containing fractions are evaporated to give an off-white solid (0.08 g).

Workup

  1. filtrationThe solid in the reaction mixture is filtered
  2. dissolutionBoth are dissolved in a MeOH
  3. customThe residue is chromatographed
  4. washeluting with 3% MeOH
  5. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-2a2c0eaa0a15403782a7b706ed4283c6
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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