Ethyl 2,3-dihydro-1H-inden-2-ylcarbamate → N-Methylindan-2-amine

HRID 327024Notes

Reaction equation

HRID 327024 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[NH:16][C:17](OCC)=O>O1CCCC1>[CH3:17][NH:16][CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 15132155Ethyl 2,3-dihydro-1H-inden-2-ylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15023225N-Methylindan-2-amineYield 221.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.13 g (30 mmol) of anhydrous lithium aluminium hydride in 150 ml of tetrahydrofuran was added a solution of 2.2 g of ethyl indan-2-carbamate in 50 ml of the same solvent. The mixture was heated to reflux, allowed to cool, hydrolysed with an excess of aqueous 1N sodium hydroxide solution, and the mixture was filtered, concentrated and distilled at about 100 Pa at 150° C. 3.5 g of oil were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationhydrolysed with an excess of aqueous 1N sodium hydroxide solution, and the mixture was filtered
  5. concentrationconcentrated
  6. distillationdistilled at about 100 Pa at 150° C

Sources & evidence

ORD record
ord-1fdb0a3978964cd2bd6416b403c87dec
Source dataset
uspto-grants-1993_12
Patent number
US05272157

Reaction notes

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