Aluminium lithium hydride → 2-NAPHTHALENAMINE, 1,2,3,4-TETRAHYDRO-N-METHYL-

HRID 1646225Notes

Reaction equation

HRID 1646225 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:11][C:12](OCC1C=CC=CC=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:12][NH:11][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54429858Benzyl 1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

Product 1

HCID 135796442-NAPHTHALENAMINE, 1,2,3,4-TETRAHYDRO-N-METHYL-Yield 112.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.43 g (26.4 mmol) of phenylmethyl 1,2,3,4-tetrahydronaphthalene-2-carbamate were added in portions to a suspension of 4.5 g (26.4 mmol) of lithium aluminium hydride in 200 ml of tetrahydrofuran and the mixture was heated to reflux for 3 h 30, allowed to cool, and hydrolysed with an excess of aqueous 1N sodium hydroxide solution, the mixture was filtered and concentrated, and the residue was distilled at about 80 Pa between 140 and 240° C. 4.78 g of impure oil were obtained, which was utilised in its impure state in the following step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h 30
  3. temperatureto cool
  4. filtrationhydrolysed with an excess of aqueous 1N sodium hydroxide solution, the mixture was filtered
  5. concentrationconcentrated
  6. distillationthe residue was distilled at about 80 Pa between 140 and 240° C

Sources & evidence

ORD record
ord-d8195d5b7dda4d5c8f0f31c082dfd204
Source dataset
uspto-grants-1993_01
Patent number
US05179108

Reaction notes

Loading…