Ethanol → Tert-butyl 8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2070124Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:5]2.C(O)C.C([O-])=O.[NH4+]>[Pd].O1CCCC1>[NH2:12][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:5]2

Participants

Conditions

Temperature: 65 °C

Procedure

tert-Butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (628 g) was added to ethanol (3.1 L), and the mixture was heated at 65° C. To the mixture, 10% Pd—C (water content: 53%) (67.1 g) and ammonium formate (1.03 kg) were sequentially added, and the resultant mixture was stirred for 10 minutes under heating and reflux. Tetrahydrofuran (2.5 L) was added to the reaction mixture so as to dissolve the precipitates, and undissolved matter was removed through filtration with Celite. The filtrate was concentrated under reduced pressure, and water was added to the residue. The formed precipitates were recovered through filtration. The thus-obtained solid was dried, whereby the title compound (418 g) was yielded as a powdery compound.

Workup

temperatureunder heating
temperaturereflux
dissolutionto dissolve the precipitates, and undissolved matter
customwas removed through filtration with Celite
concentrationThe filtrate was concentrated under reduced pressure, and water
additionwas added to the residue
customThe formed precipitates
filtrationwere recovered through filtration
customThe thus-obtained solid was dried

Sources & evidence

ORD record: ord-dff2b37bf64c47afbde109e71214a0d8
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299255B2

Reaction notes

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