Methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate → 7-amino-3-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 1038852Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][CH:14]([CH3:19])[C:15](OC)=[O:16])([O-])=O>[Pd].CC(O)(C)C>[NH2:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:13][CH:14]([CH3:19])[C:15](=[O:16])[NH:1]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A flask was charged with methyl 3-(2,4-dinitrophenyl)-2-methylpropanoate (1.1 g, 4.1 mmol), 10 wt % Pd on carbon (0.25 g, 2.3 mmol), and t-BuOH (15 mL). The mixture was degassed with H2 three times and was stirred for about 72 h at about 50° C. The mixture was filtered and the filtrate was concentrated under reduced pressure to give 7-amino-3-methyl-3,4-dihydroquinolin-2(1H)-one (0.70 g, 92%): LC/MS (Table 2, Method g) Rt=1.04 min; MS m/z: 177 (M+H)+.

Workup

customThe mixture was degassed with H2 three times
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a383f3d27f1044d7b9dec2f73b90cd29
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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