Hantzsch ester → 6-Bromo-4-hydroxy-3-(pyrimidin-5-ylmethyl)quinolin-2(1H)-one

HRID 926523Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].ClC1C2C(=CC=C([CH:25]([C:27]3[N:31]([CH3:32])[C:30](C)=[N:29][CH:28]=3)O)C=2)N=C(OC)C=1CC1C=NC(C(F)(F)F)=CC=1.N1C=C(C=O)C=NC=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>N1C=CC=CC=1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([CH2:25][C:27]1[CH:28]=[N:29][CH:30]=[N:31][CH:32]=1)=[C:5]2[OH:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a dark solution of 6-bromo-4-hydroxyquinolin-2(1H)-one (3.92 g, 16.31 mmol, Intermediate 45: step a) and pyrimidine-5-carbaldehyde (1.94 g, 17.95 mmol) in pyridine (29 mL) was added diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (4.13 g, 16.31 mol). The resulting mixture was warmed with stirring in a 100° C. oil bath for a period of 5 hours. After cooling to room temperature, the mixture was diluted with ethanol. The tan precipitate was isolated by filtration, rinsing further with EtOH then acetonitrile and dried to provide the title compound that was carried to the next step without further purification.

Workup

temperatureThe resulting mixture was warmed
temperatureAfter cooling to room temperature
customThe tan precipitate was isolated by filtration
washrinsing further with EtOH
dry with materialacetonitrile and dried

Sources & evidence

ORD record: ord-a6e1720ab1704de6a75a3c2d387ec0bd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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