Benzyl Bromide → 4-Benzyl 1-methyl 2-aminoterephthalate

HRID 1295933Notes

Reaction equation

HRID 1295933 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=O>[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 21924002HCID 21924002, compound

Product 1

HCID 107794774-Benzyl 1-methyl 2-aminoterephthalateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 1-methyl 2-aminoterephthalate (8.00 g, 41.1 mmol) in dimethylformamide (80 ml), anhydrous potassium carbonate (6.25 g, 45.1 mmol) and benzyl bromide (4.12 ml, 43.1 mmol) were added and the mixture was stirred at room temperature for 15.5 hours. An excess of triethylamine was added, and after stirring for an additional 10 minutes at room temperature, ice water was added and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with water and brine and then dried over anhydrous magnesium sulfate. Filtration was performed with silica gel-alumina and the solvent was distilled off under reduced pressure. IPE was added to the obtained oil for crystallization, and the crystals were filtered off. The filtrate was concentrated and then the same procedure was repeated twice to yield the title compound (8.21 g) as a light yellow powder.

Workup

  1. additionwere added
  2. stirringafter stirring for an additional 10 minutes at room temperature
  3. extractionextraction
  4. washThe ethyl acetate layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionIPE was added to the obtained oil for crystallization
  9. filtrationthe crystals were filtered off
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-25ee629f8619407fa5451b5545725971
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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