Hydrochloric Acid → O-(3-Carboxyphenyl)hydroxylamine

HRID 971174Notes

Reaction equation

HRID 971174 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1[CH:9]=[C:10]([O:14][NH2:15])[CH:11]=[CH:12][CH:13]=1)=[O:7].C1COCC1.CO.O.Cl>O>[C:6]([C:8]1[CH:9]=[C:10]([O:14][NH2:15])[CH:11]=[CH:12][CH:13]=1)([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 11160006HCID 11160006, compoundHCID 21892291Methanol tetrahydrofuran water

Product 1

HCID 11480924O-(3-Carboxyphenyl)hydroxylamineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LiOH.H2O (91.0 mg, 2.17 mmol) was added to a solution of O-(3-methoxycarbonyl-phenyl)hydroxylamine 14 (90.4 mg, 0.541 mmol) in a 3/1/1 mL mixture of THF/MeOH/H2O and the reaction was stirred at room temperature. After 24 h the reaction was diluted with H2O (50 mL), acidified to pH-3-4 with 0.5 N HCl, and extracted with EtOAc (3×25 mL). The combined organics were washed with H2O (25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford 3 as a white solid (78.7 mg, 95%). 1H-NMR (500 MHz, d6-DMSO) δ 7.01 (s, 2H), 7.24 (ddd, J=1.4, 2.8, 8.3 Hz, 1H), 7.34 (t, J=7.8 Hz, 1H), 7.46 (dt, J=1.4, 7.3 Hz, 1H), 7.68 (dd, J=1.4, 2.8 Hz, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 113.5, 117.8, 121.3, 129.2, 131.8, 161.7, 167.3; ESI-MS 162 m/z [M-H+]−, C7H6NO3 requires 162.

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined organics were washed with H2O (25 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a3db6b4755144686879d16a9106ca3e4
Source dataset
uspto-grants-2007_12
Patent number
US07312361B2

Reaction notes

Loading…