Sodium Nitrite → (1S,2R)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1586312Notes

Reaction equation

HRID 1586312 reaction equation
[OH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[C:11](O)=O.[N:14]([O-])=O.[Na+]>OS(O)(=O)=O>[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C@H:11]1[NH2:14]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 54248087HCID 54248087, compound

Product 1

HCID 10888251(1S,2R)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

The hydrazide of (1S,2R)-1-hydroxy-2-carboxyindane (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-hydroxy-2-aminotetralin is isolated as a light yellow oil.

Workup

  1. extractionextraction of the reaction mixture with ethyl acetate
  2. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  3. dry with materialdrying of the extracts over MgSO4, filtration
  4. customthe removal of solvent
  5. customby rotary evaporation

Sources & evidence

ORD record
ord-3691e3df783e445caca682d2471a7cd9
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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