Sulfuric Acid → HCID 23106708, compound

HRID 538330Notes

Reaction equation

HRID 538330 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[C:22](OCC)(=O)[CH3:23]>C(O)C>[CH2:22]([O:10][C:9](=[O:11])[CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)[CH3:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 29921601(2-Bromopyridin-4-yl)acetic acid

Product 1

HCID 23106708HCID 23106708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (2-bromo-pyridin-4-yl)-acetic acid (60.0 g, 277.7 mmol) in ethanol (600 ml), conc: sulfuric acid (5.0 ml) was added at rt and the reaction mixture was heated at 90° C. for 9 h. Reaction mixture was cooled to rt and concentrated under reduced pressure to remove solvent completely. The residue obtained was cooled to 0° C. and pH was adjusted to 8 using 10% aqueous NaHCO3 solution. The resultant contents were worked up with ethyl acetate by washing with water, brine and dried over anhy. Na2SO4. Organic layer was concentrated under reduced pressure to obtain crude compound. Column chromatography purification of the crude compound using 15% ethyl acetate in hexane as eluent furnished title compound as a brown oil. Yield: 65.0 g (88.5%). TLC (30% ethyl acetate in hexane) Rf=0.39; LCMS: RtH7=0.824 [M+1]+=243.8 and 245.8; HPLC RtH9=3.759 min (69%); 1H NMR (300 MHz, CDCl3): δ 8.32 (t, 1H), 7.43 (s, 1H), 7.21-7.15 (M, 1H), 4.18 (q, 2H), 1.27 (t, 3H).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to rt
  3. concentrationconcentrated under reduced pressure
  4. customto remove solvent completely
  5. customThe residue obtained
  6. temperaturewas cooled to 0° C.
  7. washby washing with water, brine
  8. customdried over anhy
  9. concentrationOrganic layer was concentrated under reduced pressure
  10. customto obtain crude compound
  11. customColumn chromatography purification of the crude compound

Sources & evidence

ORD record
ord-e203dae9a9c44fb881787e09c4eaa866
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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