Cyclohexane → HCID 178503531, compound

HRID 334389Notes

Reaction equation

HRID 334389 reaction equation
[C:1]([C:3]1[C:4]([S:13][CH3:14])=[N:5][C:6]([OH:12])=[C:7]([CH:11]=1)C(O)=O)#[N:2].C1CCCCC1>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:12][C:6]1[CH:7]=[CH:11][C:3]([C:1]#[N:2])=[C:4]([S:13][CH3:14])[N:5]=1

Participants

4

Reactant 2

HCID 8078CyclohexaneHCID 178503561HCID 178503561, compound

Product 1

HCID 178503531HCID 178503531, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 6 g (28.5 mmol) of 5-cyano-2-hydroxy-6-(methylthio)nicotinic acid in 35 ml of diphenyl ether is stirred at 250° C. for 4 hours. After returning to room temperature, 100 ml of cyclohexane is added and the reaction medium is triturated for 30 minutes. The solid formed is filtered, rinsed thoroughly with cyclohexane and then dried under vacuum to yield 2.87 g (60%) of 6-hydroxy-2-(methylthio)nicotinonitrile in the form of a brown powder.

Workup

  1. customAfter returning to room temperature
  2. customthe reaction medium is triturated for 30 minutes
  3. customThe solid formed
  4. filtrationis filtered
  5. washrinsed thoroughly with cyclohexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9c82bafac76948f78e06455e4eaaae25
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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