Nitric Acid → HCID 22992373, compound

HRID 1168422Notes

Reaction equation

HRID 1168422 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:12]([O-:15])(O)=[O:13].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([NH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:12]([O-:15])=[O:13])(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 166715-Tetralinylamine

Product 1

HCID 22992373HCID 22992373, compound

Procedure

A suspension of 1-amino-5,6,7,8-tetrahydronaphtalene (5 ml; 30 mmol) in acetic anhydride (75 ml) was stirred at ambient temperature for 30 min. After cooling to 15° C. nitric acid (1.5 ml, 65%) was added and the mixture was allowed to warm to room temperature. Stirring was continued overnight. The mixture was poured into ice-water and the oily precipitate was filtered off, washed with water and dried. This crude product was purified by column-chromatography on silica gel, using a mixture of ethyl acetate and ligroin (1:1) as the eluent. Yield: 2.5 g (30%).

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. stirringStirring
  4. waitwas continued overnight
  5. filtrationthe oily precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customThis crude product was purified by column-chromatography on silica gel
  9. additiona mixture of ethyl acetate and ligroin (1:1) as the eluent

Sources & evidence

ORD record
ord-0b35e26a82884dcd853562e3be09ca31
Source dataset
uspto-grants-2003_09
Patent number
US06624186B2

Reaction notes

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