Hydrochloric Acid → Benzene, 1-azido-3-methoxy-

HRID 614512Notes

Reaction equation

HRID 614512 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl.N([O-])=O.[Na+].[N-:15]=[N+:16]=[N-].[Na+]>O.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]=[N+:15]=[N-:16])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 542844Benzene, 1-azido-3-methoxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 9.26g. (0.08 mole) of 3-methoxyaniline in 40 ml. of water and 20 ml. of concentrated HCl was cooled to 0° C. There was then added a solution of 6.07g. (0.088 mole) of NaNO2 in 20 ml. of water, and the reaction mixture was aged for 1/2 hour. There was next added 70 ml. of hexane followed by dropwise addition of a solution of 5.72g. (0.088 mole) of NaN3 in 20 ml. of water. After addition was complete, the reaction mixture was aged for 2 hours at room temperature. The aqueous and organic components were separated and the aqueous component was extracted with 50 ml. of hexane. The hexane component and extract were dried over MgSO4 and concentrated under reduced pressure to 10.77g. (50.5%) of a yellow oil. Structure of the product as 3-methoxyphenylazide was confirmed by IR.

Workup

  1. additionThere was then added a solution of 6.07g
  2. additionThere was next added 70 ml
  3. additionAfter addition
  4. customThe aqueous and organic components were separated
  5. extractionthe aqueous component was extracted with 50 ml
  6. extractionThe hexane component and extract
  7. dry with materialwere dried over MgSO4
  8. concentrationconcentrated under reduced pressure to 10.77g

Sources & evidence

ORD record
ord-becdf44f9241416484b7f8d064a55a4b
Source dataset
uspto-grants-1979_03
Patent number
US04145364

Reaction notes

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