Hydrochloric Acid → Methyl 2-[p-(6-amino-5-fluoro-1H-benzotriazol-1-yl)phenoxy]propionate

HRID 259741Notes

Reaction equation

HRID 259741 reaction equation
Cl.C([NH:5][C:6]1[C:7]([F:28])=[CH:8][C:9]2[N:13]=[N:12][N:11]([C:14]3[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[C:10]=2[CH:27]=1)(=O)C.O>CO.S(=O)(=O)(O)O>[NH2:5][C:6]1[C:7]([F:28])=[CH:8][C:9]2[N:13]=[N:12][N:11]([C:14]3[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[C:10]=2[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19430917Methyl 2-[p-(6-acetamido-5-fluoro-1H-benzotriazol-1-yl)phenoxy]propionate

Product 1

HCID 19430911Methyl 2-[p-(6-amino-5-fluoro-1H-benzotriazol-1-yl)phenoxy]propionate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent2×

Procedure

Concentrated hydrochloric acid (6.3 mL) is added to a solution of methyl 2-[p-(6-acetamido-5-fluoro-1H -benzotriazol-1-yl)phenoxy]propionate (4.77 g, 0.013 mol) in methanol. The reaction mixture is refluxed for 18 hours, cooled to room temperature and concentrated in vacuo to obtain a solid. 1HNMR spectral analysis of the solid indicates that ester hydrolysis has occurred. A solution of the solid, sulfuric acid (4 drops) and methanol is refluxed for 6 hours, cooled to room temperature and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a brown powder which is identified by NMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. customto obtain a solid
  4. temperaturecooled to room temperature
  5. extractionThe aqueous mixture is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1654e9ed1e7f40809a51d14bbcb3eb46
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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