Hydrochloric Acid → HCID 58936500, compound

HRID 855773Notes

Reaction equation

HRID 855773 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([F:13])=[C:7]([Cl:14])[N:6]=1.Cl>O1CCOCC1>[Cl:14][C:7]1[N:6]=[C:5]([CH2:4][C:3]([OH:15])=[O:2])[C:10]([C:11]#[N:12])=[CH:9][C:8]=1[F:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58936497HCID 58936497, compound

Product 1

HCID 58936500HCID 58936500, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (6-chloro-3-cyano-5-fluoro-pyridin-2-yl)-acetic acid methyl ester (9.36 g, 40.9 mmol), as prepared in the previous step, 4.0 M HCl (aq) (256 mL) and dioxane (51 mL) was vigorously stirred at 65° C. for 2 h. The homogeneous amber solution was then allowed to cool to rt, extracted with DCM (3×100 mL), dried (Na2SO4) and concentrated under reduced pressure at 45° C. to provide the title compound as a clear, dark amber oil (7.40 g, 84%). 1H-NMR (300 MHz, CDCl3) δ 7.75 (d, 1H), 4.11 (s, 2H).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-daa3c5e514cc40e48634529eb470b88f
Source dataset
uspto-grants-2007_08
Patent number
US07262210B2

Reaction notes

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