Sodium Azide → Ethyl 4-(aminomethyl)-2-hydroxybenzoate

HRID 342827Notes

Reaction equation

HRID 342827 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([OH:14])[C:6](=[CH:12][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N-:15]=[N+]=[N-].[Na+]>CN(C)C=O.ClCCl>[NH2:15][CH2:2][C:3]1[CH:4]=[C:5]([OH:14])[C:6](=[CH:12][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 12794724Ethyl 4-bromomethylsalicylate

Product 1

HCID 12794727Ethyl 4-(aminomethyl)-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-bromomethylsalicylate (4.8 g, 18.6 mmoles) was dissolved in dry N,N-dimethylformamide (50 mL) and sodium azide (1.2 g, 18.9 mmoles) was added. The suspension was stirred at room temperature for 2 hours. The reaction mixture was then diluted with dichloromethane (150 mL) and extracted with 1N aqueous hydrochloric acid (100 mL), water (100 mL), and saturated aqueous sodium chloride(50 mL). Finally, the solution was then dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness to give ethyl 4-aminomethylsalicylate as an oil.

Workup

  1. extractionextracted with 1N aqueous hydrochloric acid (100 mL), water (100 mL), and saturated aqueous sodium chloride(50 mL)
  2. dry with materialFinally, the solution was then dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8758ecc19deb42bbb9e763ec0a7e68c2
Source dataset
uspto-grants-1999_01
Patent number
US05859210

Reaction notes

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