4-(6-Methoxy-1-methyl-2-oxo-1,2-dihydro-quinolin-4-ylamino)-piperidine-1-carboxylic acid ethyl ester → 6-Methoxy-1-methyl-4-(piperidin-4-ylamino)-1H-quinolin-2-one

HRID 897229Notes

Reaction equation

C(OC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]([CH3:25])[C:15](=[O:26])[CH:14]=2)[CH2:8][CH2:7]1)=O)C>Br.C(O)(=O)C>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:25])[C:15](=[O:26])[CH:14]=[C:13]2[NH:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(6-Methoxy-1-methyl-2-oxo-1,2-dihydro-quinolin-4-ylamino)-piperidine-1-carboxylic acid ethyl ester (445 mg, 1.2 mmol) was dissolved in HBr/Acetic acid (30% by weight HBr in Acetic Acid) and heated at 90° C. for 1 hr. The solvent was then evaporated to afford an orange solid (˜500 mg, 100%) which was carried onto the next step without any characterization.

Workup

customThe solvent was then evaporated

Sources & evidence

ORD record: ord-d84c8ff323c9415ab513dd35b75f04de
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

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