2-Methoxy-5-Methylaniline → HCID 14952458, compound

HRID 1480808Notes

Reaction equation

HRID 1480808 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:4]=1[NH2:5].[Br:11]N1C(=O)CCC1=O>CN(C=O)C.[Cl-].[Na+].O>[Br:11][C:8]1[C:7]([CH3:10])=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 2

HCID 84452-Methoxy-5-MethylanilineHCID 67184N-bromobutanimide

Product 1

HCID 14952458HCID 14952458, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a cooled (0° C.) solution of 2-methoxy-5-methylaniline (500 mg, 3.64 mmol) in DMF (5 mL) was added slowly, over 10 minutes, a solution of N-bromosuccinimide (662 mg, 3.72 mmol) in DMF (2.5 mL). The reaction mixture was stirred for 18 hours, whilst slowly warming to room temperature. The reaction mixture was diluted with brine (25 mL) and extracted with EtOAc (25 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-20% EtOAc in cyclohexane to give the title compound (679 mg, 86%). 1H NMR (500 MHz, CDCl3): δ 6.93 (s, 1H), 6.62 (d, J=0.5 Hz, 1H), 3.83 (s, 3H), 3.73 (br s, 2H), 2.26 (s, 3H).

Workup

  1. additionwas added slowly, over 10 minutes
  2. extractionextracted with EtOAc (25 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 0-20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-61a2959a5c1c4c228b25a9c1d123cfbe
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…