Nitric Acid → 7-Nitro-1-tetralone

HRID 1978002Notes

Reaction equation

HRID 1978002 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N+:12]([O-])([OH:14])=[O:13]>O>[N+:12]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][C:1]2=[O:11])=[CH:6][CH:7]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 107241-Tetralone

Product 1

HCID 384457-Nitro-1-tetralone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 1-tetralone (15.0 g, 0.103 mol) was gradually added dropwise to fuming nitric acid (100 ml). The reaction mixture was stirred for 30 minutes, which was poured into water. Resulting crystalline precipitate was collected by filtration and washed with water, which was dissolved in ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/isopropyl ether to give 7-nitro-1-tetralone. This compound was dissolved in ethanol (100 ml), to which 5% Pd.-C (50% hydrous, 1 g) was added. The mixture was stirred for 2 hours at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration, and the filtrate was concentrated. The concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 3:2), followed by recrystallization from ethyl acetate/isopropyl ether to give 1.70 g (yield from 1-tetralone, 10%) of the above-titled compound, m.p.141-143° C.

Workup

  1. temperatureUnder ice-cooling
  2. filtrationResulting crystalline precipitate was collected by filtration
  3. washwashed with water, which
  4. dissolutionwas dissolved in ethyl acetate
  5. washThe solution was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-695133adf0594683ac129e2beb5b168e
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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