Acetic Acid → HCID 43714396, compound

HRID 2208724Notes

Reaction equation

HRID 2208724 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[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>[CH:13]1([NH:1][C:2]2[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 38010253-Amino-2-methylbenzoic acid methyl esterHCID 5003444Sodium cyanoborohydride

Product 1

HCID 43714396HCID 43714396, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-2-methylbenzoate (2 g, 12.1 mmol) and cyclopentanone (5 g, 60.6 mmol) in methanol (20 mL) was added acetic acid (0.72 g, 12.12 mmol) and the reaction stirred at room temperature for 3 h. Sodium cyanoborohydride (1.13 g, 18.2 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 3-(cyclopentylamino)-2-methylbenzoate (2.2 g, 78%).

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-546f8bb8a2494531891bff9aeb68db79
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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