3-Bromo-4-ethylamino benzaldehyde → 4-Ethylamino-3-(1-ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-benzaldehyde
Reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[CH3:17].Br[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[NH:27][CH2:28][CH3:29])[CH:22]=[O:23]>>[CH2:28]([NH:27][C:26]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[CH3:17])[CH3:29]Participants
3
Procedure
The intermediate 4-ethylamino-3-(1-ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde was prepared in a similar manner to example 7a using 7-bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one (example 2b) and 3-bromo-4-ethylamino benzaldehyde. 53% yield. 1H NMR (300 MHz; CDCl3): 1.21 (t, J=6.9 Hz, 3 H), 1.31 (s, 3 H), 1.35 (s, 3 H), 2.08 (s, 3 H), 2.53 (s, 2 H), 3.27 (m, 2 H), 4.02 (q, J=7.5 Hz, 1 H), 6.75 (d, J=8.7 Hz, 1 H), 6.83 (s, 1 H), 7.21 (s, 1 H), 7.52 (s, 1 H), 7.81 (d, J=8.4 Hz, 1 H), 9.76 (s, 1 H).
Sources & evidence
- ORD record
- ord-887f63479c3548a787e47c9f7ca1b010
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07102000B2
Reaction notes
Loading…