Sodium Hydroxide → HCID 22914799, compound

HRID 542765Notes

Reaction equation

HRID 542765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:11]([C:16]#N)=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.[OH-:18].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH2:13][NH:12][C:11]=3[C:16](=[O:18])[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 139205893-[2-(4-Fluorophenyl)ethyl]pyridine-2-carbonitrile

Product 1

HCID 22914799HCID 22914799, compoundYield 64%

Procedure

The product of Step B hereof (31.5 g, 139 mmol) is cyclized in polyphosphoric acid (1.24 kg) at 200° C. for 51/2 hours. The hot reaction is poured into ice and then basified with 50% NaOH solution. The product is extracted three times with CHCl3 and then washed with brine. The organic phase is dried (Na2SO4), filtered, and solvent is removed to give the desired product (20.4 g) in 64% yield, m.p. 78°-81° C. after recrystallization from diisopropyl ether.

Workup

  1. custom2 hours
  2. customThe hot reaction
  3. additionis poured into ice
  4. extractionThe product is extracted three times with CHCl3
  5. washwashed with brine
  6. dry with materialThe organic phase is dried (Na2SO4)
  7. filtrationfiltered
  8. customsolvent is removed

Sources & evidence

ORD record
ord-d66525bc32fb48adbbea95f9173d76e6
Source dataset
uspto-grants-1987_04
Patent number
US04659716

Reaction notes

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