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

HRID 1646223Notes

Reaction equation

HRID 1646223 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-cd93cfe6c2cd480bb40c569808aa8d6c
Source dataset
uspto-grants-1993_01
Patent number
US05179108

Reaction notes

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