Anthranilic Acid → 4-Quinazolone, 2-ethyl-3-methyl

HRID 238199Notes

Reaction equation

HRID 238199 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][NH2:12].C(O[C:16](OCC)(OCC)[CH2:17][CH3:18])C.CC1C=CC(S(O)(=O)=O)=CC=1>[OH-].[Na+]>[CH2:17]([C:16]1[N:12]([CH3:11])[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1)[CH3:18]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 6329MethylamineHCID 66995Ethyl orthopropionate

Product 1

HCID 3253524-Quinazolone, 2-ethyl-3-methylYield 73%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of anthranilic acid (13.7 g, 100 mmol), methylamine (2M solution in methanol, 100 mL, 200 mmol), triethylorthopropionate (40 mL, 200 mmol), pTSA (catalytic amount) was heated at 70° C. with stirring for 3 days. The reaction mixture was cooled to room temperature, IN NaOH solution (160 mL) was added and the mixture stirred vigourously. The resulting precipitate was filtered, washed with water and dried under high vacuum to yield the product as a fluffy white solid (13.67 g, 73%). 1H NMR (400 MHz, CDCl3) δ 1.41 (t, 3H, J=7.4 Hz), 2.87 (q, 2H, J=7.4 Hz), 3.64 (s, 3H), 7.44 (t, 1H, J=8.1 Hz), 7.65 (dd, 1H, J=8.8, 0.7 Hz), 7.72 (t, 1H, J=8.4 Hz), 8.27 (dd, 1H, J=9.2, 1.8 Hz); ESI-MS m/z 189.0 (M+1)+.

Workup

  1. additionwas added
  2. stirringthe mixture stirred vigourously
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-97c11e7a34ee47ec9dd9c94908815b36
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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