Acetic Acid → HCID 70873980, compound

HRID 2208704Notes

Reaction equation

HRID 2208704 reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[C:4]([CH:9]=[C:10]([Cl: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>[Cl:13][C:3]1[C:2]([NH:1][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:11][C:10]([Cl:12])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 23714Chloramben-methylHCID 5003444Sodium cyanoborohydride

Product 1

HCID 70873980HCID 70873980, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-2,5-dichlorobenzoate (2.5 g, 11.5 mmol) and cyclopentanone (4.8 g, 57.1 mmol) in methanol (5 mL) was added acetic acid (0.6 g, 11.3 mmol) and stirring was continued at room temperature for 3 h. Then sodium cyanoborohydride (1.4 g, 22.2 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 2,5-dichloro-3-(cyclopentylamino)benzoate (0.275 g, 8%).

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-49a733748542435abeb2dc110e138f14
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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