Acetic Acid → HCID 70872494, compound

HRID 2208746Notes

Reaction equation

HRID 2208746 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[Br:12][C:10]1[CH:11]=[C:2]([NH:1][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Product 1

HCID 70872494HCID 70872494, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (1 equiv.) in methanol (5 mL), cyclopentanone (5 equiv.) and acetic acid (2 equiv.) were added and reaction mixture stirred at room temperature for 2 h. Then NaBH3CN (3 equiv.) was added at 0° C. The resulting reaction mixture was stirred further for 16 h at room temperature. On completion, solvent was evaporated and water added to the residue and the extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford crude product which was used in next step without further purification (yield 80-90%).

Workup

  1. customreaction mixture
  2. customThe resulting reaction mixture
  3. stirringwas stirred further for 16 h at room temperature
  4. customOn completion, solvent was evaporated
  5. additionwater added to the residue
  6. extractionthe extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated
  9. customto afford crude product which
  10. customwas used in next step without further purification (yield 80-90%)

Sources & evidence

ORD record
ord-bc519c8fb6ac495a98739d3359795d20
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…