Pyridine → HCID 21707201, compound

HRID 1594940Notes

Reaction equation

HRID 1594940 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[N:18]1C=CC=C[CH:19]=1.CN>C(Cl)Cl>[CH3:19][NH:18][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6329MethylamineHCID 121223'-Hydroxyphenylacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 21707201HCID 21707201, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxyphenylacetic acid (1.00 g, 6.57 mmol) and oxalyl chloride (0.63 mL, 7.22 mmol) in methylene chloride (20 mL) was treated dropwise with pyridine (0.6 mL, 7.37 mmol), stirred for 90 min, poured into 40% aqueous methylamine (30 mL), stirred for 15 min, concentrated, dissolved into 1M HCl and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with ethyl acetate to provide 260 mg of the title compound. MS (DCI/NH3) m/e 166 (M+H)+.

Workup

  1. stirringstirred for 15 min
  2. concentrationconcentrated
  3. dissolutiondissolved into 1M HCl
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-f6f054b7e0b74484a557f8392c0cc8e2
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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