Acetic Anhydride → 4-Oxo-1,4-dihydroquinazolin-6-yl acetate

HRID 2210017Notes

Reaction equation

HRID 2210017 reaction equation
[OH:1][C:2]1C=C(C(O)=O)C(N)=C[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][NH:17][C:16]2=[O:23].C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C=O)C>[C:2]([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][NH:17][C:16]2=[O:23])(=[O:1])[CH3:3]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1645925-Hydroxyanthranilic acidHCID 1354895773,4-Dihydro-6-hydroxy-4-oxoquinazoline2×

Product 1

HCID 1355842204-Oxo-1,4-dihydroquinazolin-6-yl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described in the portion of Example 1 which is concerned with the preparation of starting materials, 5-hydroxyanthranilic acid was converted into 6-hydroxyquinazolin-4-one. Acetic anhydride (1.38 g) was added dropwise to a mixture of 6-hydroxyquinazolin-4-one (2 g), triethylamine (1.37 g) and DMF (60 ml). The mixture was stirred at ambient temperature for 1 hour. The mixture was evaporated to give 6-acetoxyquinazolin-4-one which was reacted with thionyl chloride using an analogous procedure to that described in the portion of Example 1 which is concerned with the preparation of starting materials.

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-bf3c283d1e524279bc3a8551642f37fb
Source dataset
uspto-grants-1995_10
Patent number
US05457105

Reaction notes

Loading…