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

HRID 2083365Notes

Reaction equation

HRID 2083365 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-9f59fb65afe24554be85ec4d52ff35c5
Source dataset
uspto-grants-1978_04
Patent number
US04085213

Reaction notes

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