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

HRID 2172022Notes

Reaction equation

HRID 2172022 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-01d563e223aa4f4db35a06d6fde3f07b
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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