Sodium Hydroxide → 6,7-Dimethoxy-3H-quinazolin-4-one

HRID 1893876Notes

Reaction equation

HRID 1893876 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](O)=[O:5].C(O)(=O)C.[CH:19](N)=[NH:20].[OH-].[Na+]>>[CH3:14][O:13][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH3:12])[N:1]=[CH:19][NH:20][C:4]2=[O:5]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 797364,5-Dimethoxyanthranilic acidHCID 160693Formamidine acetate

Product 1

HCID 1354950166,7-Dimethoxy-3H-quinazolin-4-oneYield 76%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-amino-4,5-dimethoxybenzoic acid (1.0 g, 5.08 mmol) and formamidine acetate (4.50 g, 43.3 mmol) was disposed in a 50 mL ball. The solid mixture was heated at 140° C. in a silicone bath for eight hours. During heating, the fusion of solids happened, and then the resolidification of the reaction environment. The mixture was left cooling, and then a NaOH solution was added to it (0.33 mol.L−1) until pH was adjusted to 8. The grayish pink solid was collected through filtering in a Büchner funnel, washed with water (3×10 mL), and dried in vacuum to provide the desired compound (0.79 g, 3.83 mmol, 76%), which was used without purification in the next stage: m.p. 296-298° C. (Lit. (Bridges et al., J. Med. Chem. 1996, 39, 267), m.p. 295-298° C.).

Workup

  1. temperatureDuring heating
  2. waitThe mixture was left
  3. temperaturecooling
  4. customThe grayish pink solid was collected
  5. filtrationthrough filtering in a Büchner funnel
  6. washwashed with water (3×10 mL)
  7. customdried in vacuum

Sources & evidence

ORD record
ord-440cde4d6758469eb5561cc6ab933055
Source dataset
uspto-grants-2013_08
Patent number
US08513267B2

Reaction notes

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