Acetic Acid → HCID 54163842, compound

HRID 1417533Notes

Reaction equation

HRID 1417533 reaction equation
C(O)(=O)C.[CH3:5][C:6](=O)[CH2:7][CH2:8][C:9](=O)[CH3:10].[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[NH2:17].C(OCC)(=O)C>C1(C)C=CC=CC=1.O.O.O.C([O-])(=O)C.[Na+]>[Br:13][C:14]1[CH:15]=[C:16]([N:17]2[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]2[CH3:5])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 8857Ethyl AcetateHCID 9610833-Bromo-4-methoxyaniline

Product 1

HCID 54163842HCID 54163842, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23665404Sodium Acetate TrihydrateCatalystHCID 1140TolueneSolvent

Procedure

Using the general procedure described by S. P. Bruekelman, S. E. Leach, G. D. Meakins, and M. D. Tirel (J. Chem. Soc., Perkin Trans. 1, 1984, 2801-2807), acetic acid (0.50 mL, 0.52 g, 8.7 mmol) and sodium acetate trihydrate (70 mg, 0.51 mmol) were added to a solution of 2,5-hexanedione (8.0 mL, 7.8 g, 68 mmol) and 3-bromo-4-methoxyaniline (see Y. -Y. Lui, M. Minich, J. Labelled Compounds and Radiopharmaceuticals, 1981, 18, 791-797) in 40 mL of toluene. The mixture was heated to reflux for 2 h in a flask connected to a Dean-Stark trap. After cooling the mixture to room temperature, ethyl acetate (20 mL) was added and the solution was washed with 25 mL. each of water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give brown crystals. Recrystallization from 20 mL of warm hexane cooled to 0° C. yielded 8.17 g of tan crystals (67% yield). 1H NMR (400 MHz, CDCl3): δ 7.42 (d, 1H, J=2 Hz), 7.14 (dd, 1H, J=9, 2 Hz), 6.96 (d, 1H, J=9 Hz), 5.87 (s, 2H), 3.95 (s, 3H), 2.02 (s, 6H). Mass spectrum (NH3CI): m/e=280 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h in a flask
  3. washthe solution was washed with 25 mL
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. customdecanted
  6. customevaporated
  7. customto give brown crystals
  8. customRecrystallization from 20 mL of warm hexane
  9. temperaturecooled to 0° C.

Sources & evidence

ORD record
ord-b4060c3435c54b8683cae94ddf6afbda
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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