Hydroxylamine → HCID 136346389, compound

HRID 219842Notes

Reaction equation

HRID 219842 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[NH2:14][OH:15]>CCO>[NH2:2][C:1](=[N:14][OH:15])[C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 136346389HCID 136346389, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of methyl 5-cyano-2-hydroxy-benzoate (ASTATECH; 63806; 1 g; 5.64 mmol; 1 eq.) in EtOH (10 mL) was added hydroxylamine (50% in water) (1.69 mL; 28.22 mmol; 5 eq.). The reaction mixture was stirred at 60° C. for 30 min. While cooling to RT a white precipitate was formed. Solvents were removed to dryness and the white solids were washed with EtOH to afford title compound pure at 66% as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.12 (d, J=2.2 Hz, 1H), 7.81 (dd, J=8.4, 2.2 Hz, 1H), 6.99 (d, J=8.7 Hz, 1H), 5.82 (br s, 2H), 5.69 (br s, 1H), 3.91 (s, 3H). LC/MS (Method A): 210.8 (M+H)+.

Workup

  1. temperatureWhile cooling to RT a white precipitate
  2. customwas formed
  3. customSolvents were removed to dryness
  4. washthe white solids were washed with EtOH

Sources & evidence

ORD record
ord-e7c75ccffa504496bb9211950b48c98f
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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