Hydrochloric Acid → (E)-3-(6-aminopyridin-3-yl)2-methylacrylic acid HCl salt

HRID 2112661Notes

Reaction equation

HRID 2112661 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[ClH:16]>CC(O)=O>[ClH:16].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57440844ethyl (E)-3-(6-aminopyridin-3-yl)-2-methylacrylate

Product 1

HCID 67343937(E)-3-(6-aminopyridin-3-yl)2-methylacrylic acid HCl salt

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To ethyl (E)-3-(6-aminopyridin-3-yl)-2-methylacrylate (5.0 g, 24.2 mmole) was added HOAc (25 mL) and cone. HCl (25 mL). The reaction was stirred and heated at 100° C. for 6 hr, cooled to RT and concentrated to dryness. The remaining residue was triturated with Et2O, filtered and dried under vacuum to give the title compound (5.5 g, quantitative) as a white solid: LCMS (ES) m/e 179.0 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.47 (br s, 2H), 8.16 (d, J=1.7 Hz, 1H), 8.08 (dd, 1H), 7.42 (s, 1H), 7.08 (d, J=9.3 Hz, 1H), 2.01 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated to dryness
  3. customThe remaining residue was triturated with Et2O
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0f2c5600415344e9badcda9bdb6b0323
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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