Acetic Acid → HCID 70873949, compound

HRID 2208784Notes

Reaction equation

HRID 2208784 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, 13.01 mmol) and cyclopentanone (5.6 g, 66 mmol) in methanol (30 mL), acetic acid (1.59 g, 26.6 mmol) was added and the reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (2.08 g, 29.4 mmol) was added and the mixture stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford methyl 2-bromo-3-(cyclopentylamino)benzoate (1.4 g, 36%).

Workup

  1. stirringthe mixture stirred overnight
  2. customOn completion, solvent was removed under reduced pressure and crude material
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3c67077241c24c69afff455f6c4a1736
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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