3-Bromo-o-toluidine → Methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoate

HRID 661820Notes

Reaction equation

HRID 661820 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Br:15][C:16]1[C:17]([CH3:23])=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>CO.C(Cl)Cl>[Br:15][C:16]1[C:17]([CH3:23])=[C:18]([NH:19][CH2:2][C:3]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:4]=2[C:5]([O:7][CH3:8])=[O:6])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 1235383-Bromo-o-toluidineHCID 53407594Methyl 2-(bromomethyl)-5-methoxybenzoate

Product 1

HCID 66606189Methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoateYield 18%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

Step 2 A mixture of methyl 2-(bromomethyl)-5-methoxybenzoate (1.435 g, 5.54 mmol), 3-bromo-2-methylaniline (1.03 g, 5.54 mmol) and TEA (1.158 mL, 8.31 mmol) in methanol (5 mL) was heated at 85° C. for 2 h. The mixture was diluted with DCM, washed with NaHCO3 (aq), and dried and concentrated. The residue was purified by column chromatography (eluting with EtOAc-hexane) to provide methyl 2-((3-bromo-2-methylphenylamino)methyl)-5-methoxybenzoate as a yellow oil (361 mg, 18%). Mass spectrum m/z 364, 366 (M+H)+.

Workup

  1. washwashed with NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (eluting with EtOAc-hexane)

Sources & evidence

ORD record
ord-502aa1e8077a4ebd80501260a3a61fef
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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