Methanol → HCID 67776917, compound

HRID 511646Notes

Reaction equation

HRID 511646 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH3:16])[CH2:15][CH2:14][CH2:13]2)=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18])=O.CO.C(=O)([O-])[O-].[K+].[K+].O>>[CH3:16][C:12]1([C:9]2[CH:10]=[CH:11][C:6]([NH2:5])=[C:7]([N+:17]([O-:19])=[O:18])[CH:8]=2)[CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 86666125HCID 86666125, compound

Product 1

HCID 67776917HCID 67776917, compoundYield 102.1%

Conditions

Temperature
45 °C

Procedure

A solution of 2,2,2-trifluoro-N-[4-(1-methylcyclobutyl)-2-nitrophenyl]acetamide (580 mg. 1.9 mmol) in Methanol (18 ml, 440 mmol) was treated with a solution of Potassium carbonate (788 mg, 5.70 mmol) in Water (4.5 ml, 250 mmol) and the mixture was heated at 45° C. for 50 minutes The reaction mixture was cooled to RT and the methanol was removed in vacuo. The remaining aqueous phase was diluted with 10 ml H2O and extracted with three 20 ml portions of EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated to yield an oil. The material was placed on high vacuum where upon it solidified giving the desired compound (400 mg). The material was used directly in the next step 1H NMR (400 MHz. CDCl3) d ppm 7.90 (d, J=2.07 Hz, 1H), 7.23 (dd, J=8.50, 2.28 Hz, 1H), 6.77 (d, J=8.71 Hz, 1H), 5.96 (br. s., 2H), 2.33 (m, 2H), 2.13 (m, 1H), 2.04 (m, 2H), 1.84 (m, 1H), 1.43 (s, 3H).

Workup

  1. temperaturewas cooled to RT
  2. customthe methanol was removed in vacuo
  3. additionThe remaining aqueous phase was diluted with 10 ml H2O
  4. extractionextracted with three 20 ml portions of EtOAc
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil

Sources & evidence

ORD record
ord-1258c160a7a34ae0a8db5d51f322a4c6
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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