Hydrochloric Acid → 6-Amino-5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazole

HRID 259745Notes

Reaction equation

HRID 259745 reaction equation
[F:1][C:2]1[C:18]([NH:19]C(=O)C)=[CH:17][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])[N:7]=[N:8][C:4]=2[CH:3]=1.Cl.[OH-].[Na+].O>C(O)C.C(Cl)Cl.C(OCC)(=O)C>[NH2:19][C:18]1[C:2]([F:1])=[CH:3][C:4]2[N:8]=[N:7][N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])[C:5]=2[CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15346066N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]acetamide

Product 1

HCID 153460676-Amino-5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazole

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[5-fluoro-1-(o-methoxyphenyl)-1H -benzotriazol-6-yl]acetamide (7.14 g, 0.024 g) and concentrated hydrochloric acid (18 mL) in ethanol is refluxed for 2 hours, cooled to room temperature, brought to about pH 5.5 with 3M sodium hydroxide solution and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark, brown oil. Flash column chromatography of the oil using silica gel and 5% to 10% ethyl acetate in methylene chloride solutions gives the title product as an orange solid, mp 128°-129° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a dark, brown oil

Sources & evidence

ORD record
ord-43d77437cc514ac4a0d74b9bd067666f
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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