Acetylacetone → 8-Chloro-2-methyl-10-(trifluoromethyl)-pyrimido[5,4-b]quinolin-4(3H)-one

HRID 456979Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:17]([NH2:19])=[O:18])=[N:4][C:5]2[C:10]([C:11]=1[C:12]([F:15])([F:14])[F:13])=[CH:9][C:8]([Cl:16])=[CH:7][CH:6]=2.[C:20](CC(=O)C)(=O)[CH3:21]>OS(O)(=O)=O>[Cl:16][C:8]1[CH:7]=[CH:6][C:5]2[N:4]=[C:3]3[C:17](=[O:18])[NH:19][C:20]([CH3:21])=[N:1][C:2]3=[C:11]([C:12]([F:13])([F:15])[F:14])[C:10]=2[CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Amino-6-chloro-4-(trifluoromethyl)-2-quinolinecarboxamide (12, 172 mg, 0.594 mmol) was dissolved acetylacetone (5.9 mL). Three drops of H2SO4 were added and the reaction was heated to 100° C. for 30 minutes. The reaction was cooled to rt and the copious cream precipitate was collected and washed with cold CH3OH to provide the desired product (103 mg, 55%) requiring no further purification. 1H NMR (d6-DMSO, 300 MHz) δ12.73 (br s, NH), 8.35 (d, J=9.2 Hz, 1 H), 8.29 (s, 1H), 7.97 (dd, J=2.2, 9.1 Hz, 1H), 2.44 (s, 3H); 19F NMR (CDCl3, 300 MHz) δ−51.34; IR (KBr) νmax 3442, 3060, 2920, 1706, 1629, 1608, 1560, 1485, 1336, 1329, 1198, 1144, 1114, 961, 837, 710 cm−1.

Workup

temperatureThe reaction was cooled to rt
customthe copious cream precipitate was collected
washwashed with cold CH3OH

Sources & evidence

ORD record: ord-f9e9af43e4ea411299bb6c58156548ff
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186830B2

Reaction notes

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