O-Xylene → HCID 58574369, compound

HRID 1619388Notes

Reaction equation

HRID 1619388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]=[C:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])[CH:3]=1.C1(C)C(C)=CC=CC=1>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:11](=[O:15])[C:10]([CH2:14][CH2:13][OH:12])=[CH:9][N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 7237O-XyleneHCID 67258003HCID 67258003, compound

Product 1

HCID 58574369HCID 58574369, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a small flask, 3-((4-bromopyridin-2-ylamino)methylene)dihydrofuran-2(3H)-one (250 mg, 0.93 mmol) and CF3COOH (8 drops) was added into a solution of xylene. The suspension was warmed to 85° C. and maintained at that temperature for 30 min. After the upper layer of suspension was poured out, the residue was diluted with water (30 mL) and adjusted to pH 8. Then the mixture was extracted with ethyl acetate (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography. MS (ESI): 269, 271 (MH+).

Workup

  1. temperaturemaintained at that temperature for 30 min
  2. additionAfter the upper layer of suspension was poured out
  3. extractionThen the mixture was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-038597f2811b4a0f948da99fbc0ac9ef
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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