Nitric Acid → 6-Acetamido-5-nitro-1-tetralone

HRID 979811Notes

Reaction equation

HRID 979811 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].[OH-].[Na+]>>[C:1]([NH:4][C:5]1[C:6]([N+:16]([O-:18])=[O:17])=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 140052246-Acetamido-5-nitro-1-tetralone

Conditions

Temperature
0 °C

Procedure

6-Acetamido-tetralone (15 g) was added in small portions to a cold solution of nitric acid (46 ml) at -30° C. After the addition was complete (2-3 hours), the reaction mixture was stirred at the same temperature for 1 hour, warmed to 0° C. and stirred for 4 hours. The reaction was poured on ice, basified with aqueous sodium hydroxide and extracted with ethyl acetate several times. The organic layer was separated, dried and evaporated. The desired 5-nitro-isomer was separated using flash chromatography (ethyl acetate-methylene chloride) to afford 8.73 g (48%).

Workup

  1. additionAfter the addition
  2. custom(2-3 hours)
  3. stirringstirred for 4 hours
  4. additionThe reaction was poured on ice
  5. extractionextracted with ethyl acetate several times
  6. customThe organic layer was separated
  7. customdried
  8. customevaporated
  9. customThe desired 5-nitro-isomer was separated
  10. customto afford 8.73 g (48%)

Sources & evidence

ORD record
ord-184ba6ff82044428970c6657972fd2e0
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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