Aluminium lithium hydride → 6-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine

HRID 1385896Notes

Reaction equation

HRID 1385896 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21716276HCID 21716276, compound

Product 1

HCID 199076-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (30 mmol) of 2-azido-6-methoxytetralin 15 ml of TMF were added dropwise in the course of 15 minutes at 0° C. to a suspension of 1.7 g (44 mmol) of lithium aluminum hydride in 70 ml of THF. The mixture was stirred for 30 minutes at room temperature and refluxed for 1 hour. After cooling to 0° C., excess alanate was destroyed with isopropanol, and the mixture was diluted with ether and washed with saturated tartrate and saturated NaCl solution. After the organic phase had been dried and concentrated, the resulting colorless oil was further employed directly. Yield 5.1 g (96% of theory).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling to 0° C.
  3. customexcess alanate was destroyed with isopropanol
  4. additionthe mixture was diluted with ether
  5. washwashed with saturated tartrate and saturated NaCl solution
  6. customAfter the organic phase had been dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5aa983a0e4d24230b7bbb2818ad6c951
Source dataset
uspto-grants-2001_07
Patent number
US06265398B1

Reaction notes

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