Sodium Azide → 2-Azido-4-nitrobenzyl alcohol

HRID 650512Notes

Reaction equation

HRID 650512 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[N-:22]=[N+:23]=[N-].[Na+]>Cl.O.O>[N:1]([C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])=[N+:22]=[N-:23]

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 541982-Amino-4-nitrobenzyl alcoholHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 867572472-Azido-4-nitrobenzyl alcoholYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21885828Hydrate;hydrochlorideSolvent

Procedure

To a suspension of 2-amino-4-nitrobenzyl alcohol [(0.5 g) Bio. Org. Med. Chem (1995) 3, 2, 129] in concentrated hydrochloric acid/H2O (15 ml of 1:1 v:v) at −50 to 0° was added a solution of sodium nitrite (0.24 g) in water (2.5 ml) dropwise so the temperature did not rise above 0°. The mixture was stirred for 10 min, and added dropwise to a cooled (0°) solution of sodium acetate (3.0 g) and sodium azide (0.2 g) in water (10 ml). The resulting solid was filtered, washed with water and dried on the sinter to give the title compound as a pale brown powder (0.45 g, 78%). δH (d6 DMSO): 4.51 (2H, s), 5.52 (1H, br), 7.72 (1H, d, J 8.4 Hz), 7.99 (1H, d, J 2.2 Hz) and 8.04 (1H, dd, J 2.2, 8.4 Hz) .

Workup

  1. customdid not rise above 0°
  2. additionadded dropwise to
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried on the sinter

Sources & evidence

ORD record
ord-880195bf9f2d4183924f5a97064d83a8
Source dataset
uspto-grants-2001_08
Patent number
US06274577B1

Reaction notes

Loading…