Acetic Acid → HCID 70873993, compound

HRID 2208789Notes

Reaction equation

HRID 2208789 reaction equation
[NH2:1][C:2]1[C:3]([Cl: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.C([BH3-])#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]([Cl:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 63022790HCID 63022790, compound

Product 1

HCID 70873993HCID 70873993, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-chlorobenzoate (2.8 g, 10.6 mmol) and cyclopentanone (4.47 g, 53.2 mmol) in methanol (20 mL) was added acetic acid (1.3 mL, 21.2 mmol) and the reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.7 g, 26.6 mmol) was added and the reaction stirred overnight. On completion, the solvent was removed under reduced pressure and the product was purified by column chromatography to afford methyl 5-bromo-2-chloro-3-(cyclopentylamino)benzoate (0.5 g, 14.2%).

Workup

  1. stirringthe reaction stirred overnight
  2. customOn completion, the solvent was removed under reduced pressure
  3. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-2f8c32062a064fd5bc0a603c1ffa29c4
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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