Cyclohexane → HCID 178503531, compound

HRID 1487360Notes

Reaction equation

HRID 1487360 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-39754df6f5074d1c8016097b6832d611
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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