Hydrochloric Acid → 5-Bromo-4-methoxy-2-methylaniline

HRID 1661969Notes

Reaction equation

HRID 1661969 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

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66766852HCID 66766852, compound

Product 1

HCID 667671595-Bromo-4-methoxy-2-methylanilineYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureAfter being heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc (1200 mL)
  4. customThe organic phase is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94e8432259714e7ea5444731554ddfd3
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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