Sodium Acetate → 2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 888105Notes

Reaction equation

HRID 888105 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:3]=1[C:4]([N:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:7][C:8]([CH3:10])=[CH2:9])=[O:5].C(O[Na])=O.CC([O-])=O.[Na+]>CN(C=O)C.[N+](CC)(CC)(CC)CC.[Cl-]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:6]2[CH2:7][C:8]([CH3:10])([CH3:9])[C:2]3[C:3](=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)[C:4]2=[O:5])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 219593762-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamideHCID 178526064HCID 178526064, compound

Product 1

HCID 219593622-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamide (23.4 mmol) was dissolved in DMF (150 ml) and Et4NCl (4.25 g), HCO2Na (1.75 g) and NaOAc (4.99 g) were added. N2 was bubbled through the solution for 10 min, then Pd(OAc)2 (490 mg) was added and the mixture was stirred overnight at 70° C. The mixture was extracted with EtOAc, washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated until the compound precipitated as a white solid.

Workup

  1. customN2 was bubbled through the solution for 10 min
  2. additionPd(OAc)2 (490 mg) was added
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated until the compound
  8. customprecipitated as a white solid

Sources & evidence

ORD record
ord-f7bb1f0a7be84792988ebb1a0c339977
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

Loading…