4-Bromoaniline → HCID 59020725, compound

HRID 1846305Notes

Reaction equation

HRID 1846305 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[NH:9]C(=O)O[C:12](=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>CN(C=O)C>[NH2:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[C:12]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([Br:15])=[CH:17][CH:18]=1)=[O:13]

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 105596798-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 59020725HCID 59020725, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (1.50 g, 7.70 mmol) and 4-bromoaniline (1.40 g, 8.10 mmol) in anhydrous DMF (10 mL) was stirred at 115° C. for 16 hours under nitrogen. DMF was removed and the residue was mixed with water (100 mL) and ethyl acetate (150 mL). The organic phase was separated and washed with brine (50 mL). The solvent was removed and the residue was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give 2-amino-N-(4-bromo-phenyl)-3-methoxy-benzamide. Yield: 1.49 g (60%).

Workup

  1. customDMF was removed
  2. additionthe residue was mixed with water (100 mL) and ethyl acetate (150 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-18573cf0d5c046dc9790e35aff6b488b
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…