4-Bromoaniline → HCID 54877884, compound

HRID 1846302Notes

Reaction equation

HRID 1846302 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[NH:7]C(=O)O[C:10](=[O:11])[C:5]=2[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>[NH2:7][C:6]1[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:10]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([Br:15])=[CH:17][CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 54877884HCID 54877884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (0.800 g, 4.10 mmol) and 4-bromoaniline (0.750 g, 4.30 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, backwashed with brine (50 mL), and concentrated. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give 2-amino-N-(4-bromo-phenyl)-5-methoxy-benzamide. Yield: 0.240 g (18%).

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. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-169d41a81c0d4adfa5684387faa38a96
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…