Ammonium Acetate → HCID 59321495, compound

HRID 2423533Notes

Reaction equation

HRID 2423533 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([O:8][C:9](=[O:23])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[C:20](=O)[CH3:21])=O)[CH3:7]>C(O)(=O)C>[Br:19][C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][CH:17]=1)[N:12]=[C:10]([C:9]([O:8][CH2:6][CH3:7])=[O:23])[N:5]=[C:20]2[CH3:21]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 59321497Ethyl [(2-acetyl-4-bromophenyl)amino](oxo)acetate

Product 1

HCID 59321495HCID 59321495, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ammonium acetate (400.0 mg, 5.19 mmol) was added to ethyl[(2-acetyl-4-bromophenyl)amino](oxo)acetate (163.0 mg, 518.9 μmol) in acetic acid (5.2 mL) at room temperature and the reaction was heated at reflux for 19 hours. The reaction mixture was concentrated, then water was added, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 2:3 ethyl acetate:hexanes to give 75.5 mg (49%) of ethyl 6-bromo-4-methyl-2-quinazolinecarboxylate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 8.63 (d, J=2 Hz, 1H), 8.21 (dd, J=9, 2 Hz, 1H), 8.07 (d, J=9 Hz, 1H), 4.41 (q, J=7 Hz, 2H), 2.97 (s, 3H), 1.35 (t, J=7 Hz, 3H). ESI-LCMS m/z 295 (M+H)+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 19 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added
  5. extractionthe solution was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 2:3 ethyl acetate

Sources & evidence

ORD record
ord-a4f4a14886514799bed8c0f4e266fc68
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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