Acetic Acid → HCID 67281854, compound

HRID 1616150Notes

Reaction equation

HRID 1616150 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])[C:5]([O:7][CH3:8])=[O:6].C(O)(=O)C.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C.[O-2].[Mn+4].[O-2]>[CH:15]([N:14]1[C:12](=[O:13])[C:11]2[C:2](=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=2)[N:1]=[C:22]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 67283096HCID 67283096, compound

Product 1

HCID 67281854HCID 67281854, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 3-amino-4-[(isopropylamino)carbonyl]benzoate (15 mg, 0.07 mmol) in ethanol (1.5 mL) was added acetic acid (32 μL, 0.56 mmol) and benzaldehyde (19.4 μL, 0.19 mmol). The reaction mixture was heated to 110° C. and stirred overnight. The mixture was then concentrated to dryness and taken up in chloroform (1 mL). To this solution was added manganese (IV) oxide (28 mg, 0.32 mmol) and the reaction mixture was heated to 110° C. and stirred for 2 d. The reaction mixture was then filtered through Celite, rinsed with chloroform and concentrated to dryness to afford methyl 3-isopropyl-4-oxo-2-phenyl-3,4-dihydroquinazoline-7-carboxylate. LC-MS: (FA) ES+ 323.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. temperaturethe reaction mixture was heated to 110° C.
  3. stirringstirred for 2 d
  4. filtrationThe reaction mixture was then filtered through Celite
  5. washrinsed with chloroform
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d816691ec02f40a3917851db6e6aec75
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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