2-Methoxyethylamine → HCID 68308665, compound

HRID 922445Notes

Reaction equation

HRID 922445 reaction equation
[CH2:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:5]=2[C:3](=[O:4])[CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][O:27][CH2:28][CH2:29][NH2:30]>CN(C)C=O.ClCCl>[CH3:26][O:27][CH2:28][CH2:29][NH:30][C:11]([C:9]1[CH:10]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH2:1][CH2:2][C:3]2=[O:4])=[O:13]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 123412861-Indanone-6-carboxylic acid

Product 1

HCID 68308665HCID 68308665, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-indanone-6-carboxylic acid (1.76 g) in N,N-dimethylformamide (50 mL) was added carbonyldiimidazole (3.24 g), and the mixture was stirred at room temperature for 1 hour. Thereto was added a solution of 2-methoxyethylamine (3.76 g) in dichloromethane (50 mL) under ice cooling, and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and then dissolved in chloroform. The organic layer was washed with aqueous saturated sodium hydrogen carbonate solution, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (20 mL), and then thereto was added 1-normal hydrochloric acid (20 mL), and the mixture was stirred at room temperature for 12 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether-ethyl acetate (2:1) to give N-(2-methoxyethyl)-3-oxoindan-5-carboxamide [REx(13-1)] (1.87 g) as a brown powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutiondissolved in chloroform
  4. washThe organic layer was washed with aqueous saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe resulting residue was dissolved in tetrahydrofuran (20 mL)
  8. additionwas added 1-normal hydrochloric acid (20 mL)
  9. stirringthe mixture was stirred at room temperature for 12 hours
  10. additionTo the reaction solution was added water
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with saturated saline
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe resulting residue was triturated with isopropyl ether-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-a0aa885f9bad4e79a75fd3ac5cce01e5
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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