Trifluoroacetic acid → HCID 86083508, compound

HRID 2367140Notes

Reaction equation

HRID 2367140 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]#[CH:18])[C:5]([CH3:16])=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]#[CH:18])[C:5]([CH3:16])=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86617522HCID 86617522, compound

Product 1

HCID 86083508HCID 86083508, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (5-chloro-3-ethynyl-2-methylphenyl)carbamate (242 mg, 0.91 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (500 μl). The solution was stirred at ambient temperature for 1 hour. The solution was partitioned between saturated sodium bicarbonate and dichloromethane. The aqueous layer was extracted twice with dichloromethane. The combined organic portions were washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford an orange oil which was purified by column chromatography (silica gel, 50% dichloromethane in hexane). The product was collected to afford 60 mg, 0.36 mmol (40%) of 5-chloro-3-ethynyl-2-methylaniline as a white solid. 1H NMR (400 MHz, CDCl3): 6.90 (d, 1H), 6.63 (d, 1H), 3.71 (br s, 2H), 3.24 (s, 1H), 2.23 (s, 3H); MS (EI) for C9H8ClN: 166 (MH+).

Workup

  1. customThe solution was partitioned between saturated sodium bicarbonate and dichloromethane
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customto afford an orange oil which
  8. customwas purified by column chromatography (silica gel, 50% dichloromethane in hexane)
  9. customThe product was collected

Sources & evidence

ORD record
ord-045f514652374537a0e60464065ccdf8
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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