Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate
Reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2].[NH2:15][OH:16]>CCO>[NH2:2][C:1](=[N:15][OH:16])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of methyl 4-cyano-3-methoxybenzoate, obtained in step 1 (135 mg; 0.71 mmol; 1 eq.) in EtOH (1.35 mL) was added hydroxylamine (50% in water) (0.21 mL; 3.53 mmol; 5 eq.). The reaction mixture was stirred at 60° C. for 3 h. Solvent were removed to dryness, to afford the title compound as a white powder (191 mg; quantitative). 1H NMR (DMSO-d6, 300 MHz) δ 9.58 (br s, 1H), 7.56-7.51 (m, 3H), 5.71 (br s, 2H), 3.87-3.85 (m, 6H). HPLC (Method A), Rt 1.17 min (purity: 95.0%).
Workup
- customSolvent were removed to dryness
Sources & evidence
- ORD record
- ord-335d11da82e543acbc9699b8082412de
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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