2-Amino-5-chlorobenzoic acid → 4(3H)-Quinazolinone, 6-chloro-3-methyl-

HRID 1507642Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:12][NH:13][CH:14]=O>O>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:12][N:13]([CH3:14])[C:4]2=[O:5]

Participants

Conditions

Temperature: 180 °C

Procedure

2-amino-5-chlorobenzoic acid 27 (12.5 g, 73 mmol) was placed in a 250 mL beaker containing n-methylformamide (125 mL). A condenser was utilized and the reaction was heated overnight at 180° C. The reaction was complete the next morning and allowed to cool to room temperature for 1 hr and then poured into 500 mL of water and extracted three times with 250 mL of ethyl acetate. The organic phase was then washed with an additional 1 liter of water and concentrated under vacuum to yield 6-chloro-3-methylquinazolin-4(3H)-one (9.2 g, 47.3 mmol, 65% yield) 1H NMR (300 MHz, D6 DMSO): δ 8.39 (s, 1H), 8.04 (d, 1H, J=3.6 Hz), 7.82 (dd, 1H, J=2.4 Hz, J=8.7 Hz), 7.67 (1H, d, J=8.7 Hz), 3.49 (s, 3H). 13C NMR (75 MHz, D6 DMSO): δ 160.49, 149.75, 147.65, 135.06, 131.99, 130.26, 125.61, 123.45, 34.53. ESMS: m/z 195.2 [MH]+

Workup

customA condenser was utilized
temperatureto cool to room temperature for 1 hr
extractionextracted three times with 250 mL of ethyl acetate
washThe organic phase was then washed with an additional 1 liter of water
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ea2ea80c7d324d3eb2c44421b542d7f0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221805B2

Reaction notes

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