Hydrochloric Acid → 6,7-Dimethoxyquinazoline-2,4(1H,3H)-dione

HRID 579731Notes

Reaction equation

HRID 579731 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[C-:16]#[N:17].[K+].[OH-:19].[Na+].S(=O)(=O)(O)O>O1CCCC1.O>[CH3:14][O:13][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH3:12])[NH:1][C:16](=[O:19])[NH:17][C:4]2=[O:6]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 797364,5-Dimethoxyanthranilic acid

Product 1

HCID 1200816,7-Dimethoxyquinazoline-2,4(1H,3H)-dioneYield 54.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

21 g of 2-Amino-4,5-dimethoxy benzoic acid was dissolved in 40 ml of tetrahydrofuran and 40 ml of water. To this solution 10 ml of conc. hydrochloric acid and 11.6 g of potassium cyanide were added. It was left to stand overnight and 50 g of sodium hydroxide was added. After stirring for 2 hours, the resulting precipitate was isolated by filtration. The precipitate was dissolved in 1000 ml of water and acidified with 50% sulfuric acid. The resulting crystal was isolated by filtration and 13.0 g of the desired compound was obtained. m.p. 320° C. (decomp).

Workup

  1. waitIt was left
  2. customthe resulting precipitate was isolated by filtration
  3. customThe resulting crystal was isolated by filtration

Sources & evidence

ORD record
ord-76d5bbb2a31649f3aea0d966c00686c5
Source dataset
uspto-grants-1988_06
Patent number
US04749705

Reaction notes

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