Hydrochloric Acid → 5-Methoxy-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

HRID 1608055Notes

Reaction equation

HRID 1608055 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[BH3-]C#[N:16].[Na+].[ClH:18]>CO>[ClH:18].[NH2:16][CH:8]1[CH2:7][CH2:6][CH2:5][C:4]2[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 366205-MethoxytetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 703499325-Methoxy-1,2,3,4-tetrahydronaphthalen-1-amine hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mmol of 5-methoxy-1-tetralone, 0.5 mol of NH4OAc and 35 mmol of NaBH3CN are stirred in 150 ml of absolute MeOH at room temperature for 24 hours. The mixture is acidified to pH 2 with concentrated HCl and evaporated, the residue is taken up in 50 ml of H2O and the mixture is extracted by shaking 2-3×with ether. Any precipitates which arise are filtered off and combined with the H2O phase. The H2O phase is brought to pH 10 with solid KOH, saturated with NaCl and extracted by shaking 3×with ethyl acetate. After drying with Na2SO4, the organic phase is evaporated, the residue is dissolved in ether and the product is precipitated as the hydrochloride by passing the HCl. Yield: 79%; melting point: 250° C.

Workup

  1. customevaporated
  2. extractionthe mixture is extracted
  3. customAny precipitates which
  4. filtrationarise are filtered off
  5. extractionextracted
  6. stirringby shaking 3×with ethyl acetate
  7. dry with materialAfter drying with Na2SO4
  8. customthe organic phase is evaporated
  9. dissolutionthe residue is dissolved in ether
  10. customthe product is precipitated as the hydrochloride

Sources & evidence

ORD record
ord-83541631c07f4385bf643250a6c21ee3
Source dataset
uspto-grants-1989_09
Patent number
US04868331

Reaction notes

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