Water → 3-chloro-2-(N,N-dimethylaminooxycarbonyl)phenol

HRID 1463450Notes

Reaction equation

HRID 1463450 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:11])[C:7]=1[C:8]([OH:10])=[O:9].Cl.[CH3:13][N:14]([CH3:16])O.C(N(CC)CC)C.O>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][N:14]([CH3:16])[CH3:13])=[O:9])=[C:6]([OH:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 925912-Chloro-6-hydroxybenzoic acid

Product 1

HCID 190904833-chloro-2-(N,N-dimethylaminooxycarbonyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.73 Grams of 6-chlorosalicylic acid was dissolved in 20 ml of tetrahydrofuran, and 1.95 g of N,N'-carbonyldiimidazole was added. After stirring at room temperature for 30 minutes, 1.47 g of N,N-dimethylhydroxylamine hydrochloride and 1.52 g of triethylamine were added, and the resulting mixed solution was stirred at room temperature for 7 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained was subjected to column chromatography to obtain 1.1 g of 3-chloro-2-(N,N-dimethylaminooxycarbonyl)phenol.

Workup

  1. additionthe resulting mixed solution
  2. stirringwas stirred at room temperature for 7 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue obtained

Sources & evidence

ORD record
ord-7c011f4180094b6ea42c1874ff8c216a
Source dataset
uspto-grants-1994_04
Patent number
US05300640

Reaction notes

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