Acetic Acid → HCID 70873949, compound

HRID 2208781Notes

Reaction equation

HRID 2208781 reaction equation
[NH2:1][C:2]1[C:3]([Br:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:12][C:3]1[C:2]([NH:1][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 13574117Methyl 3-amino-2-bromobenzoate

Product 1

HCID 70873949HCID 70873949, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-2-bromobenzoate (3 g, 13.0 mmol) and cyclopentanone (5.4 g, 64.28 mmol) in methanol (20 mL), acetic acid (1.56 g, 26 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (2 g, 31.7 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material purified by column chromatography to afford methyl 2-bromo-3-(cyclopentylamino)benzoate (1.4 g, 36%).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-a9b04f80406d4e2eb35603e314ddb958
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…