Hydroxyamine hydrochloride → HCID 86727013, compound

HRID 1770635Notes

Reaction equation

HRID 1770635 reaction equation
C([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)=O.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)(C)C.O>[OH:18][N:17]=[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH2:4]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 85843028HCID 85843028, compound

Product 1

HCID 86727013HCID 86727013, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of methyl 4-formyl-2-nitrobenzoate (2.0 g, 9.4 mmol) in isopropanol (50 ml) and water (25 ml) was treated with hydroxylamine hydrochloride (0.7 g) and sodium acetate (0.72 g) and stirred for 2 hours at room temperature. The solvent was then evaporated and the residue was treated with water (25 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over sodium sulfate and concentrated to give methyl 4-hydroxylimino-2-nitrobenzoate (1.8 g). 1H-NMR (400 MHz, CDCl3): 11.90 (1H, s), 8.20 (1H, d), 8.00 (1H, d), 7.89 (1H, d), 3.85 (3H, s) ppm.

Workup

  1. customThe solvent was then evaporated
  2. additionthe residue was treated with water (25 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea031e2dfdf84a2791f777151cb98b56
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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