Beta-Alanine → HCID 404684, compound

HRID 1597125Notes

Reaction equation

HRID 1597125 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10].NC[CH2:13][C:14]([OH:16])=[O:15]>>[C:14]([CH2:13][CH2:9][N:4]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:10])([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 239Beta-AlanineHCID 2972Deferiprone

Product 1

HCID 404684HCID 404684, compound

Procedure

A reaction analogous to that used for the synthesis of 3-hydroxy-1,2-dimethyl-4-pyridinone was employed starting with β-alanine (2.5 g). No precipitate was observed after concentration and, at this point, the pH was set to 4 with hydrochloric acid. Following extraction with dichloromethane, the solvent was removed by rotary evaporation. Hydrogenolysis was performed as before, although the final product was not recrystallized. An off-white powder was obtained (2.3 g). Proton NMR (D20): 7.89 (d, 1H), 6.88 (d, 1H), 4.39 (t, 2H), 2.76 (t, 2H), 2.38 (s, 3H).

Workup

  1. customA reaction analogous to
  2. concentrationafter concentration
  3. extractionextraction with dichloromethane
  4. customthe solvent was removed by rotary evaporation
  5. customwas not recrystallized
  6. customAn off-white powder was obtained (2.3 g)

Sources & evidence

ORD record
ord-2c8fd281962f432891bed871d0e97b12
Source dataset
uspto-grants-2001_09
Patent number
US06294152B1

Reaction notes

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