Hydroxylamine → Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoate

HRID 219853Notes

Reaction equation

HRID 219853 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[NH2:15][OH:16]>CCO>[NH2:2][C:1](=[N:15][OH:16])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 2801011Methyl 3-cyano-4-methoxybenzoate

Product 1

HCID 53410613Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoateYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-cyano-4-methoxybenzoate (518 mg, 2.71 mmol), hydroxylamine (810 μL, 50% in water, 13.55 mmol) in EtOH (20 mL) was heated for 18 h at 60° C. after which time solvents were removed under vacuum, solid residue was triturated with water filtered and dried under vacuum overnight to give the title compound as an off-white solid (600 mg, quant). 1H NMR (DMSO-d6, 300 MHz) δ 9.48 (s, 1H), 7.97-7.95 (m, 2H), 7.20-7.17 (m, 1H), 5.70 (bs, 2H), 3.87 (s, 3H), 3.82 (s, 3H). LC/MS (Method B): 225.1 (M+H)+.

Workup

  1. customwere removed under vacuum, solid residue
  2. customwas triturated with water
  3. filtrationfiltered
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-a4dfb99051f8486d833d4003466f4670
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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