Ammonium Acetate → 2-Methyl-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid

HRID 2369812Notes

Reaction equation

[CH3:1][C:2]1[O:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=O)[C:4]=2[N:3]=1.C([O-])(=O)C.[NH4+:20]>[NH4+].[OH-].CO>[CH3:1][C:2]1[NH:20][C:13](=[O:15])[C:12]2[C:4](=[C:5]([C:6]([OH:7])=[O:8])[CH:9]=[CH:10][CH:11]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Methyl-4-oxo-4H-3,1-benzoxazine-8-carboxylic acid (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

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

Sources & evidence

ORD record: ord-09bfe4a83d1b46d1a507739bab649db1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710044B2

Reaction notes

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