2-Aminobenzyl alcohol → 2-Azidobenzenemethanol

HRID 1266333Notes

Reaction equation

HRID 1266333 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N([O-])=O.[Na+].[N-:14]=[N+:15]=[N-].[Na+]>FC(F)(F)C(O)=O.O>[N:1]([C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])=[N+:14]=[N-:15]

Participants

6

Reactant 3

HCID 214392-Aminobenzyl alcoholHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 124917242-AzidobenzenemethanolYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-aminobenzyl alcohol (12.0 g, 97.4 mmol) in 50 mL of trifluoroacetic acid at 0° C. was added sodium nitrite (7.39 g, 107.2 mmol). This solution was stirred for 45 min and then there was added sodium azide (6.33 g, 97.4 mmol) dropwise as a solution in water. The resulting mixture was stirred at 0° C. for 45 min and then was carefully quenched by slow addition of potassium carbonate. The reaction mixture was diluted with ethyl acetate, washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 10.5 g (72%) of the title compound which was used without further purification. 1H NMR (CDCl3) δ7.33 (m, 2H), 7.14 (m, 2H), 4.59 (s, 2H), 2.69 (broad s, 1H).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 45 min
  2. customwas carefully quenched by slow addition of potassium carbonate
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0765ea9e4fe446580ee02a221c6e556
Source dataset
uspto-grants-2003_04
Patent number
US06548525B2

Reaction notes

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