Hydroxyamine hydrochloride → Methyl 5-[(hydroxyimino)methyl]-2-methoxybenzoate

HRID 391392Notes

Reaction equation

HRID 391392 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:17][N:16]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10856352Methyl 5-formyl-2-methoxybenzoate

Product 1

HCID 58993456Methyl 5-[(hydroxyimino)methyl]-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 5-formyl-2-methoxybenzoate 1.0 g, 5.15 mmol), hydroxylamine hydrochloride (1.8 g, 25.75 mmol) and sodium acetate (2.1 g, 25.75 mmol) were combined in a ethanol/water mixture (1:1, 40 mL) and stirred at 50° C. for 1 h. After cooling to room temperature, the reaction mixture was poured in to ice water and extracted with methylene chloride (2×). The combined organic layers were washed with brine (2×), dried over sodium sulfate and concentrated to afford 1.04 g (97%) which was used without purification. LC/MS (HPLC method 3): tR=1.63 min, 210.06 (MH)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with methylene chloride (2×)
  3. washThe combined organic layers were washed with brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford 1.04 g (97%) which
  7. customwas used without purification

Sources & evidence

ORD record
ord-53ef901096d240aebc8d4684c167382c
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

Loading…