Trifluoroacetic acid → 4-Amino-3-hydroxybenzonitrile

HRID 413340Notes

Reaction equation

HRID 413340 reaction equation
C(CC(O[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=1[OH:18])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH2:9])=[C:11]([OH:18])[CH:12]=1)#[N:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53741421N-t-butylacetoxy-4-cyano-2-hydroxyl aniline

Product 1

HCID 101977194-Amino-3-hydroxybenzonitrileYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-t-butylacetoxy-4-cyano-2-hydroxyl aniline (3.1 g, 13 mmol) in methylene chloride (100 mL) at 0° C. was added trifluoroacetic acid and the reaction mixture was allowed to warm to rt. After 2.5 h, the reaction was quenched with water (100 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash column chromatography (50% ethyl acetate/hexanes) to give 1.7 g (96%) of 4-cyano-2-hydroxyl aniline as a tan solid. 1H NMR (400 MHz, DMSO) δ 7.0 (d, 1H), 6.85 (s, 1H), 6.65 (d, 1H); MS(EI) m/e 134 (M+).

Workup

  1. customthe reaction was quenched with water (100 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash column chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-55c87892fa3448afb4f443676d6b3454
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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