Hydrochloric Acid → (E)-3-(6-aminopyrid-3-yl)acrylic acid hydrochloride

HRID 82966Notes

Reaction equation

HRID 82966 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12]C(C)(C)C)=[O:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[ClH:24]>C(Cl)Cl.O1CCOCC1>[ClH:24].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57777730HCID 57777730, compound

Product 1

HCID 66967187(E)-3-(6-aminopyrid-3-yl)acrylic acid hydrochlorideYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (2E)-3-(6-aminopyridin-3-yl)acrylate (380 mg, 1.73 mmol; which may be prepared as described in Step 1) in DCM (3.45 mL) under Argon was added trifluoroacetic acid (3.45 mL). The mixture was stirred at room temperature for 1 h, then HCl 4N in dioxane (6.9 mL) was added. A beige solid started precipitating at the half of the addition. After concentration, the solid was triturated in Et2O, filtered, rinsed with Et2O and dried under vacuum to give the title compound as a beige solid (265 mg, 76%).

Workup

  1. customA beige solid started precipitating at the half of the addition
  2. concentrationAfter concentration
  3. customthe solid was triturated in Et2O
  4. filtrationfiltered
  5. washrinsed with Et2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-808c4508cb314fa4a11ce97799b66d97
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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