Thionyl Chloride → HCID 22612156, compound

HRID 844056Notes

Reaction equation

HRID 844056 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH:2]=1.S(Cl)(Cl)=O.[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1>>[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 773174-PyridinemethanamineHCID 22032862HCID 22032862, compound

Product 1

HCID 22612156HCID 22612156, compound

Procedure

A solution of 2-(Pyridin-3-yloxy)-nicotinic acid (0.0664 grams, 0.31 mmole) in thionyl chloride (1.12 ml, 15.4 mmole) was heated to 50° C. After 1.5 hours the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Pyridine (2.5 ml) was added followed by C-Pyridin-4-yl-methylamine (47 μl, 0.47 mmole) at room temperature. After 2 hours the mixture was concentrated to remove pyridine. The crude product was purified by chromatography on silica gel eluting with 9/1 ethyl acetate/methanol to give a solid. (0.0331 g). M.P. 142-144° C.; Anal. calcd. for C17H14N4O2: C, 66.66; H, 4.61; N, 18.29. Found: C, 66.40; H, 4.56; N, 17.94.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionPyridine (2.5 ml) was added
  3. concentrationAfter 2 hours the mixture was concentrated
  4. customto remove pyridine
  5. customThe crude product was purified by chromatography on silica gel eluting with 9/1 ethyl acetate/methanol
  6. customto give a solid

Sources & evidence

ORD record
ord-fecdf2e6444c4216bea1d0ac242dad1d
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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