Phenol → 8-METHYLQUINAZOLINE-2,4(1H,3H)-DIONE

HRID 1391306Notes

Reaction equation

HRID 1391306 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](O)=[O:6])[C:3]=1[NH2:11].[NH2:12][C:13](N)=[O:14].C1(O)C=CC=CC=1>C(O)C>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[NH:11][C:13](=[O:14])[NH:12][C:5]2=[O:6]

Participants

5

Reactant 3

HCID 996PhenolHCID 1176UreaHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 3340238-METHYLQUINAZOLINE-2,4(1H,3H)-DIONEYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

3-Methylanthranilic acid (15 g., 0.1 mole), urea (36 g., 0.6 mole) and phenol (86 g.) were mixed together and heated to reflux for three hours. The reaction was then allowed to cool to 100° C. and ethanol (75 ml.) added dropwise. The resulting solid was filtered and washed twice with cold ethanol to afford 13.2 g. (75% yield); m.p. 170° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. filtrationThe resulting solid was filtered
  4. washwashed twice with cold ethanol
  5. customto afford 13.2 g

Sources & evidence

ORD record
ord-104550f892264f24a7d56e5275ddc131
Source dataset
uspto-grants-1979_02
Patent number
US04141979

Reaction notes

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