Nitric Acid → 4-Aminoadamantan-1-ol

HRID 1424576Notes

Reaction equation

HRID 1424576 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[N+]([O-])(O)=[O:13].[OH-].[Na+]>OS(O)(=O)=O>[NH2:1][CH:2]1[CH:3]2[CH2:11][C:7]3([OH:13])[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 253322-Aminoadamantane

Product 1

HCID 28574474-Aminoadamantan-1-olYield 14%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 2-aminoadamantane (10 g, 54 mmol) was added H2SO4 (150 mL) and HNO3 (15 ml) at 0° C. and the mixture was stirred overnight. The mixture was poured onto ice and adjusted to pH=10-11 using 40% aq NaOH under ice bath. The mixture was extracted with CH2Cl2. The organic layer was dried, filtered and concentrated to give 4-aminoadamantan-1-ol (3.0 g, 14%).

Workup

  1. additionThe mixture was poured onto ice
  2. extractionThe mixture was extracted with CH2Cl2
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5c0e91ed2fa4b3abc0f320cfc394e3f
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…