Ammonium Acetate → 4-Oxo-3,4-dihydroquinazoline-8-carboxylic acid

HRID 1842857Notes

Reaction equation

HRID 1842857 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:6]=2[N:5]=[CH:4]O1.C([O-])(=O)C.[NH4+:19]>[NH4+].[OH-].CO>[O:1]=[C:2]1[C:7]2[C:6](=[C:11]([C:12]([OH:14])=[O:13])[CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][NH:19]1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 676086644-oxo-4H-3,1-benzoxazine-8-carboxylic acid

Product 1

HCID 1357422154-Oxo-3,4-dihydroquinazoline-8-carboxylic acidYield 17,529.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

4-oxo-4H-3,1-benzoxazine-8-carboxylic acid derivative (51.5 g; 251.26 mmol) was dissolved in NH4OH (360.0 ml; 6.98 V; 28% solution). Ammonium acetate (77.5 g; 1.005 mmol) was added, and the reaction mixture was heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with MeOH (40 mL) then heated for 72 h at 80° C. in a pressure bottle. The reaction mixture was concentrated on the rotary evaporator then cooled on ice and filtered. The solid was dried under vacuum to provide the desired product (33.5 g, 65% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperaturethen heated for 72 h at 80° C. in a pressure bottle
  3. concentrationThe reaction mixture was concentrated on the rotary evaporator
  4. temperaturethen cooled on ice
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-297a8036aeba4de4a5771dbdef9ed81d
Source dataset
uspto-grants-2015_02
Patent number
US08946247B2

Reaction notes

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