Ethyl orthoformate → 3-Amino-4(3H)-quinazolinone

HRID 1197445Notes

Reaction equation

HRID 1197445 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[CH:12](OCC)(OCC)OCC>C(O)C>[NH2:7][N:6]1[C:4](=[O:5])[C:3]2[C:2](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:1]=[CH:12]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 94728Benzoic acid, 2-amino-, hydrazide

Product 1

HCID 631253-Amino-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-aminobenzhydrazide (7.16 g, 47.4 mmol) and triethyl orthoformate (8.3 mL, 49.9 mmol) in ethanol is heated at reflux for 3.5 hours under a nitrogen atmosphere, cooled and filtered to obtain the title product as a white solid, 6.06 g (79%), mp 209°-210.5° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3.5 hours under a nitrogen atmosphere
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-db61151175604882a3da7076350c92bf
Source dataset
uspto-grants-1994_01
Patent number
US05276038

Reaction notes

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