Acetonitrile → methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate

HRID 1616126Notes

Reaction equation

HRID 1616126 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[C:16](#[N:18])[CH3:17]>Cl.O1CCOCC1>[CH3:17][C:16]1[NH:18][C:4](=[O:6])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 135890465methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of dimethyl 2-aminoterephthalate (0.50 g, 2.4 mmol) in 4.0 M hydrochloric acid in 1,4-dioxane (4.8 mL) was added acetonitrile (1.0 mL, 19.0 mmol). The reaction mixture was heated to 50° C. and stirred for 3 h. The mixture was then cooled to rt, concentrated and the residue was twice co-evaporated with toluene. Ether was added and the mixture was extracted with water (2×). The combined aqueous phases were then concentrated to afford methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.52 g, quant). LC-MS: (FA) ES+ 219.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. additionEther was added
  4. extractionthe mixture was extracted with water (2×)
  5. concentrationThe combined aqueous phases were then concentrated

Sources & evidence

ORD record
ord-12e6ff76f728468aba47a778d170e46a
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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