2-AMINO-4-METHOXY-BENZOICACID

Yellow powder

Intermediate 113: 2-Amino-4-methoxybenzoic acid4-Methoxy-2-nitrobenzoic acid (3 g, 16.4 mmol) was hydrogenated over palladium on carbon (10percent, 300 mg) in methanol (80 mL) at room temperature and normal pressure for 18 hours. The reaction mixture was filtered through celite and concentrated to dryness under reduce pressure to give 2.50 g (100percent) of the product as a colorless solid.Example 33. Preparation of 2-(4-(2-hydroxyethoxy)-3, 5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-oneExample 28 Method 30; 2-Amino-4-methoxy benzoic acid; A mixture of 4-methoxy-2-nitrobenzoic acid (20 g, 101.5 mmol), 10percent Pd/C (1.5 g) in MeOH (200 ml) was stirred at 25 °C under a hydrogen atmosphere for 168 h. The mixture was diluted with MeOH and filtered through diatomaceous earth. The organics were removed under reduced pressure to yield a light brown solid (14.85 g, 87.6percent). NMR: 7.65 (d, IH), 6.30 (s, IH), 6.15 (d, IH), 3.80 (s, 3H); m/z 167.Compounds 1-3 were made using similar procedures to those in U. S. Patent No. 4, 287, 341 which is herein incorporated by reference in its entirety for all purposes as if fully set forth herein. Compound 3 was reduced using standard hydrogenation conditions of 10percent Pd/C in NH40H at 50 C over 48 hours. The product was precipitated by neutralizing with glacial acetic acid, filtering, and washing with water and ether. Yields were about 50percent. Compound 5 was prepared in a manner similar to that disclosed in U. S. Patent No. 5, 716, 993 herein incorporated by reference in its entirety for all purposes as if fully set forth herein.

Molecular Weight:167.16
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:167.058243149
Monoisotopic Mass:167.058243149
Topological Polar Surface Area:72.6
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes