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

HRID 633922
Notes
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Reaction equation

HRID 633922 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57777730Tert-butyl 3-(6-aminopyridin-3-yl)prop-2-enoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 31275
1,4-Dioxane
Solvent

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-66bf979289be4381900ec5d4788c634f
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321769B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes