Methanol → Methyl 4-(aminocarbonyl)-3-methylbenzoate

HRID 735727Notes

Reaction equation

HRID 735727 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(N(CC)CC)C.[CH3:19][OH:20].CN([CH:24]=[O:25])C>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:8][C:6]([C:5]1[CH:9]=[CH:10][C:2]([C:19]([O:25][CH3:24])=[O:20])=[CH:3][C:4]=1[CH3:11])=[O:7]

Participants

8

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 206167664-Bromo-2-methylbenzamide

Product 1

HCID 20642852Methyl 4-(aminocarbonyl)-3-methylbenzoateYield 70%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-bromo-2-methylbenzamide (1.65 g, 7.75 mmol), triethylamine (2.17 ml, 15.5 mmol), palladium acetate (0.0873 g, 0.388 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.215 g, 0.388 mmol), methanol (5 ml) and DMF (15 ml) was stirred under a carbon monoxide atmosphere at 70° C. for 22 hrs. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried (over anhydrous MgSO4). After concentration under reduced pressure, the obtained crystals were recrystallized from ethyl acetate to give the title compound (1.05 g, 70%) as a pale-brown needle.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried (over anhydrous MgSO4)
  4. concentrationAfter concentration under reduced pressure
  5. customthe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ac2fb812649a459a83967540f6670c96
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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