Hydrazine hydrate (1:1) → O-((4-Methoxyphenyl)methyl)hydroxylamine
Reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.O.NN>CO>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][NH2:9])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 2-(4-methoxybenzyloxy)isoindoline-1,3-dione (200 mg, 0.706 mmol) in MeOH (5 mL) was added hydrazine monohydrate (35.3 mg, 0.706 mmol). The reaction mixture was stirred at 65° C. for 1 h. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc (5 mL). After stirring for 20 min, the mixture was filtered. The filtrate was concentrated in vacuo to afford the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.30 (m, 2H), 6.90 (m, 2H), 4.63 (m, 2H), 3.81 (s, 3H).
Workup
- customThe solvent was removed in vacuo
- additionthe resulting residue was diluted with EtOAc (5 mL)
- stirringAfter stirring for 20 min
- filtrationthe mixture was filtered
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-a77a861e76664f0bb782daf9a39910e0
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410264B2
Reaction notes
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