Hydrochloric Acid → (E)-3-(6-Amino4-methylpyridin-3-yl)acrylic acid HCl salt

HRID 225884

Reaction equation

HRID 225884 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12]CC)=[O:11])=[C:4]([CH3:15])[CH:3]=1.[ClH:16]>CC(O)=O>[ClH:16].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57440845Ethyl (E)-3-(6-amino-4-methylpyridin-3-yl)acrylate

Product 1

HCID 67343018(E)-3-(6-Amino4-methylpyridin-3-yl)acrylic acid HCl salt

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To ethyl (E)-3-(6-amino-4-methylpyridin-3-yl)acrylate (1.50 g, 7.3 mmole) was added HOAc (15 mL) and conc. HCl (15 mL). The solution was stirred at 100° C. for 10 hr, cooled to RT, and concentrated to dryness. Trituration with Et2O, filtration and drying under vacuum gave the title compound (1.65 g, quantitative) as a white solid: LCMS (ES) m/e 179.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1 H), 8.28 (br s, 3 H), 7.51 (d, J=16.0 Hz, 1 H), 6.86 (s, 1 H), 6.46 (d, J=16.0 Hz, 1 H), 2.41 (s, 3 H).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated to dryness
  3. filtrationTrituration with Et2O, filtration
  4. customdrying under vacuum

Sources & evidence

ORD record
ord-26b1e53b2cb842a89693c3990bacc8da
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Linked notes

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