Hydrochloric Acid → 5-Bromo-4-methoxy-2-methylaniline
Reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8]C(=O)C)[CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:7]=1)[NH2:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-(5-bromo-4-methoxy-2-methylphenyl)acetamide (108 g, 0.42 mol) in MeOH (400 mL) is added concentrated HCl (160 mL, 2 mol). After being heated at reflux overnight, the mixture is neutralized with aqueous NaHCO3, and extracted with EtOAc (1200 mL). The organic phase is dried and concentrated to afford the product (76 g, 84% yield). MS (m/z): 216.0 (M+H).
Workup
- temperatureAfter being heated
- temperatureat reflux overnight
- extractionextracted with EtOAc (1200 mL)
- customThe organic phase is dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-94e8432259714e7ea5444731554ddfd3
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030302B2
Reaction notes
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