Hydrochloric Acid → HCID 15221722, compound

HRID 857284Notes

Reaction equation

HRID 857284 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([I:11])[CH:5]=1.N([O-])=O.[Na+].Cl.[N-:18]=[N+:19]=[N-].[Na+]>O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N+:18]=[N-:19])=[C:6]([I:11])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 4104649Methyl 4-amino-3-iodobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 15221722HCID 15221722, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of the 4-amino-3-iodo-benzoic acid methyl ester from Step 1 (1.0 eq) in water (0.36M) was added NaNO2 (1.2 eq). The resulting mixture was cooled to 0° C. and aqueous HCl (6M; 2.5 eq) was added dropwise over 45 min. The mixture was stirred at 0° C. for 4 h, then NaN3 (1.1) dissolved in water (1.0M) was added over 30 min. The final mixture was stirred at room temperature for 1 h and extracted with Et2O (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 4:1) afforded the desired compound as a light brown solid.

Workup

  1. additionwas added over 30 min
  2. extractionextracted with Et2O (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7a1bc09cc4d40a4b650782abeec3a8c
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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