Acetic Acid → HCID 86719542, compound

HRID 2208750Notes

Reaction equation

HRID 2208750 reaction equation
[NH2:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[C:15]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:13][C:10]1[C:11]([CH3:12])=[C:2]([NH:1][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:3]([CH3:14])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 86719543HCID 86719543, compound

Product 1

HCID 86719542HCID 86719542, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2,4-dimethylbenzoate (1.4 g, 5.42 mmol) and cyclopentanone (2.4 mL, 27.13 mmol) in methanol (20 mL), acetic acid (0.650 g, 10.84 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.85 g, 13.56 mmol) was added and reaction was stirred for overnight. On completion, solvent was removed water was added and compound was extracted with ethyl acetate. Combined organic layer was collected, dried over Na2SO4 and concentrate under reduced pressure and crude material was purified by column chromatography to afford the desired compound (1.2 g, 68%).

Workup

  1. customreaction
  2. customreaction
  3. stirringwas stirred for overnight
  4. customOn completion, solvent was removed water
  5. additionwas added
  6. extractioncompound was extracted with ethyl acetate
  7. customCombined organic layer was collected
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrate under reduced pressure and crude material
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-98062f7698564684bc4fdccf17d5bc99
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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