Dimethylformamide → HCID 23020169, compound

HRID 917392Notes

Reaction equation

HRID 917392 reaction equation
CN(C)C=O.Cl[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1.[CH2:16]([OH:20])[C:17]#[C:18][CH3:19].[H-].[Na+]>C(O)(=O)C>[CH2:16]([O:20][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1)[C:17]#[C:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 792226-Chloronicotinic acid

Product 1

HCID 23020169HCID 23020169, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 70 ml of N,N-dimethylformamide, 3.00 g (19 mmol) of 6-chloronicotinic acid and 2.00 g (29 mmol) of 2-butyne-1-ol were dissolved, followed by adding 1.80 g (45 mmol) of 60% sodium hydride, stirring at room temperature for 1 hour and stirring at 140° C. for 3 hours. The reaction liquid was then poured in 150 ml of ice water, and acetic acid was added to make pH 5, followed by adding 50 ml of a saturated saline solution. The crystal precipitated was filtered, washed with cold water and hexane and dried to obtain 0.96 g (yield: 26%) of 6-(2-butynyloxy)nicotinic acid.

Workup

  1. stirringstirring at 140° C. for 3 hours
  2. customThe reaction liquid
  3. customThe crystal precipitated
  4. filtrationwas filtered
  5. washwashed with cold water and hexane
  6. customdried

Sources & evidence

ORD record
ord-35435fa4ff8548afb89de5e734fad886
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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