Nitric Acid → 4-Aminoadamantan-1-ol

HRID 1506252Notes

Reaction equation

HRID 1506252 reaction equation
S(=O)(=O)(O)O.[N+]([O-])(O)=O.[CH:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH:11]1[NH2:20])[CH2:17]2.[OH-:21].[Na+]>O>[NH2:20][CH:11]1[CH:12]2[CH2:18][C:16]3([OH:21])[CH2:15][CH:14]([CH2:19][CH:10]1[CH2:17]3)[CH2:13]2

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 253322-Aminoadamantane

Product 1

HCID 28574474-Aminoadamantan-1-olYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (35 mL) was mixed with concentrated nitric acid (4.5 mL) and 2-adamantylamine (5.10 g, 4.57 mmol) under cooling with ice, and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was added to ice water and adjusted to pH 10 with 7.5 M aqueous sodium hydroxide. After addition of water, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound as a yellow solid (2.79 g, yield 61%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4975ef3813d848daa6cb4b8344e35615
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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