Sodium Hydroxide → 7-Methylquinazoline-2,4(1H,3H)-dione

HRID 2062198Notes

Reaction equation

HRID 2062198 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[O-:12][C:13]#[N:14].[K+].[OH-].[Na+]>O.C(O)(=O)C>[CH3:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:14][C:13](=[O:12])[NH:1]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 753164-Methylanthranilic acidHCID 11378442Potassium cyanate

Product 1

HCID 148599897-Methylquinazoline-2,4(1H,3H)-dioneYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 2-amino-4-methylbenzoic acid (58.9 g, 390 mmol) in water (1.5 L) and glacial acetic acid (50 ml) was added dropwise a solution of potassium cyanate (80.5 g, 993 mmol) in water (300 ml). After completion of the addition and stirring at room temperature for half an hour, sodium hydroxide pellets (500 g) were added at such a rate that the temperature was kept below 50° C. (with ice cooling). During the addition the mixture became a clear solution for a short period, and upon continuation of the sodium hydroxide addition a cream precipitate started forming. The suspension was cooled to 0-5° C. and the precipitate was collected by filtration and washed twice with water (150 ml). The solid was poured in water (1 L) and was acidified with concentrated aqueous HCl (30%, 150 ml). The solid was collected by filtration and washed with water (150 ml) to yield 7-methylquinazoline-2,4(1H,3H)-dione (57.0 g, 83%) after drying at 45° C. under vacuum.

Workup

  1. additionAfter completion of the addition
  2. customwas kept below 50° C.
  3. additionDuring the addition the mixture
  4. customstarted forming
  5. temperatureThe suspension was cooled to 0-5° C.
  6. filtrationthe precipitate was collected by filtration
  7. washwashed twice with water (150 ml)
  8. additionThe solid was poured in water (1 L)
  9. filtrationThe solid was collected by filtration
  10. washwashed with water (150 ml)

Sources & evidence

ORD record
ord-c486936cd95a47f8b474e0b73f6860a1
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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