Pyridine → HCID 76653341, compound

HRID 1437122Notes

Reaction equation

HRID 1437122 reaction equation
[CH:1]([O:4][C:5](=[O:16])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=1)([CH3:3])[CH3:2].Cl.[NH2:18][OH:19].N1C=CC=CC=1>CO>[CH:1]([O:4][C:5](=[O:16])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[N:18][OH:19])[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 57940803HCID 57940803, compound

Product 1

HCID 76653341HCID 76653341, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-formyl phenoxy)acetic acid isopropyl ester (3.7 g, 17 mmol) in methanol (55 mL) was stirred under nitrogen as hydroxylamine hydrochloride (1.2 g, 17 mmol) and pyridine (6 mL, 74 mmol) were added. The reaction was stirred for 15 h at room temperature. The volatiles were removed in vacuo and the residue was diluted with ethyl acetate. The resulting solution was washed with 1N HCl, and the resulting aqueous solution was washed with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (4.13 g, 100%) as a pale yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (d, 6H) 4.67-4.72 (m, 2H) 5.15-5.34 (m, 1H) 7.01-7.07 (m, 1H) 7.33-7.36-7.43 (m, 2H) 8.17 (s, 1H). LRMS m/z calcd. for C12H15NO4([M+H]+): 237.1. Found: 238.1.

Workup

  1. additionwere added
  2. customThe volatiles were removed in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washThe resulting solution was washed with 1N HCl
  5. washthe resulting aqueous solution was washed with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-784a4651472443c9bdb618656673f26d
Source dataset
uspto-grants-2009_11
Patent number
US07622475B2

Reaction notes

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