3-Bromo-o-toluidine → HCID 66605859, compound

HRID 661822Notes

Reaction equation

HRID 661822 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C[Al](C)C.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[N:25])[CH:22]=2)[CH2:17][O:16]1>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:15](=[O:14])[C:23]2[CH:22]=[C:21]([C:24]#[N:25])[CH:20]=[CH:19][C:18]=2[CH2:17][OH:16])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1235383-Bromo-o-toluidineHCID 132895623-Oxo-1,3-dihydro-2-benzofuran-5-carbonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 66605859HCID 66605859, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Step 1 A solution of 3-bromo-2-methylaniline (0.67 g, 3.60 mmol) in DCM (18 mL) was treated dropwise with trimethylaluminum (2 M in toluene, 1.801 mL, 3.60 mmol) and the resulting solution was stirred at rt for 30 min. A solution of 3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile (0.573 g, 3.60 mmol) in DCM (18.00 mL) was added and the resulting mixture was stirred at rt overnight. The mixture was diluted with DCM, washed with an aqueous solution of sodium potassium tartrate (Fehling's Reagent II) and water, then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to provide N-(3-bromo-2-methylphenyl)-5-cyano-2-(hydroxymethyl)benzamide as a white solid (170 mg, 14%) which was used without further purification. Mass spectrum m/z 345, 347 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at rt overnight
  2. washwashed with an aqueous solution of sodium potassium tartrate (Fehling's Reagent II) and water
  3. customwas dried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

Sources & evidence

ORD record
ord-de5b68f09dab4ed583c98ee5615747e4
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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