Acetyl chloride → Methyl 5-amino-2-bromobenzoate

HRID 1888366Notes

Reaction equation

HRID 1888366 reaction equation
[C:1](Cl)(=O)C.C([NH:8][C:9]1[CH:10]=[CH:11][C:12]([Br:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])(=O)C>CO>[CH3:1][O:16][C:14](=[O:15])[C:13]1[CH:17]=[C:9]([NH2:8])[CH:10]=[CH:11][C:12]=1[Br:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27341595-Acetamido-2-bromobenzoic acid

Product 1

HCID 245495Methyl 5-amino-2-bromobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (29.2 ml, 32.2 g, 410.7 mmol) was added dropwise to methanol (210 ml) at 0-10° C. under nitrogen atmosphere and the solution was stirred for 30 min at 0° C. After addition of 5-acetamido-2-bromobenzoic acid (21.2 g, 82.1 mmol) in methanol at 0° C. the solution was stirred for 3 h at 55° C. After evaporation of methanol ethyl acetate (160 ml) was added and stirring was continued for 1 h at room temperature. The precipitation was filtered off and it was dissolved in water. pH was adjusted to 8 with NaHCO3. The mixture was extracted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under vacuum.

Workup

  1. stirringwas stirred for 3 h at 55° C
  2. customAfter evaporation of methanol ethyl acetate (160 ml)
  3. additionwas added
  4. stirringstirring
  5. waitwas continued for 1 h at room temperature
  6. customThe precipitation
  7. filtrationwas filtered off
  8. dissolutionit was dissolved in water
  9. extractionThe mixture was extracted with ethyl acetate
  10. washwashed with water
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-04cf396dcfcf42eb87ffb4b2efba58d4
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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