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

HRID 327026Notes

Reaction equation

HRID 327026 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-b3239afd700e47c39a0af1e6bb6e6498
Source dataset
uspto-grants-1993_12
Patent number
US05272157

Reaction notes

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