Sodium Hydroxide → 1-Aminotetralin, (S)-

HRID 1606788Notes

Reaction equation

HRID 1606788 reaction equation
C(N[C@@H](C(O)=O)CCC(O)=O)(=O)C1C=CC=CC=1.[C@@H:19]1([NH2:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>O>[C@@H:19]1([NH2:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70616871HCID 70616871, compound

Product 1

HCID 70580741-Aminotetralin, (S)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A slurry of 130.3 grams (0.36 mole) of (S)-1,2,3,4-tetrahydro-1-naphthylamine N-benzoyl-(R)-glutamic acid salt in ice and water is made basic by the addition of a cold solution of 34.0 grams (0.847 mole) of sodium hydroxide in water. The liberated amine is extracted with ether. The ether solution is dried over a mixture of magnesium sulfate and sodium hydroxide pellets. The ether is evaporated, and the amine distilled to give the product boiling point 72°C. to 77°C. at 0.6 mm, [α]D25 + 54.9° (c 5.2, benzene).

Workup

  1. extractionThe liberated amine is extracted with ether
  2. dry with materialThe ether solution is dried over a mixture of magnesium sulfate and sodium hydroxide pellets
  3. customThe ether is evaporated
  4. distillationthe amine distilled

Sources & evidence

ORD record
ord-fa55a27f7e304b81aee9decba741f09b
Source dataset
uspto-grants-1976_04
Patent number
US03953606

Reaction notes

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