Hydrochloric Acid → 5-Amino-3,4-dihydronaphthalen-1(2H)-one

HRID 719170Notes

Reaction equation

HRID 719170 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.Cl.[N:13]([O-])=O.[Na+].[N-:17]=[N+:18]=[N-:19].[Na+]>O>[NH2:13][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:3]=1[CH2:2][CH2:1][CH2:11][C:9]2=[O:10].[N:17]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:3]=1[CH2:2][CH2:1][CH2:11][C:9]2=[O:10])=[N+:18]=[N-:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 107241-TetraloneHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 2

HCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-oneHCID 218968435-Azido-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

5-Amino-1-tetralone was prepared from α-tetralone according to the literature (J. Am. Chem. Soc. 1994, p4852). To a cold solution of 5-amino-1-tetratone (415 mg) in water (2 mL) and concentrated hydrochloric acid (5 mL) was added a solution of sodium nitrite (186 mg) in water (1.2 mL), maintaining low temperature. After 40 minutes a solution of sodium azide (184 mg) in water (1.2 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature. After one further hour the reaction was quenched with water, extracted into ether, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo to yield crude material which was purified using flash chromatography to yield 5-azido-1-tetralone (77 mg).

Workup

  1. temperaturemaintaining low temperature
  2. customAfter one further hour the reaction was quenched with water
  3. extractionextracted into ether
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto yield crude material which
  8. customwas purified

Sources & evidence

ORD record
ord-8b43ea73b55143e7b5f0d2d6afb116f7
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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