Hydrochloric Acid → Ethyl 4-(4'-amino-3-methyl-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:24])[CH2:9][CH:10]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>[Fe].C(O)C.O>[NH2:31][C:28]1[CH:27]=[CH:26][C:25]([C:4]2[CH:5]=[CH:6][C:7]([C:8](=[O:24])[CH2:9][CH:10]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:2]([CH3:1])[CH:3]=2)=[CH:30][CH:29]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of ethyl 4-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (3.40 g, 7.60 mmol), iron powder (4.20 g, 76.00 mmol), 2 N aqueous hydrochloric acid (3.80 mL, 7.60 mmol), and 85/15 ethanol/water (100 mL) was stirred at reflux for 2.5 h. The reaction mixture was filtered through a pad of Celite®, and concentrated to give ethyl 4-(4′-amino-3-methyl-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate as a light, brown solid (2.94 g, 93% yield). LC-MS ret. time 3.23 min, m/z 416.1 (MH+); 1H NMR (CDCl3) δ 1.32 (t, 3H), 1.82-2.17 (m, 2H), 2.58 (s, 3H), 2.68-2.77 (m, 2H), 2.98-3.09 (m, 2H), 3.49 (dd, 1H), 3.74 (br s, 2H), 4.10 (q, 2H), 6.79 (d, 2H), 7.12-7.37 (m, 5H), 7.38-7.54 (m, 4H), 7.78 (d, 1H).
Workup
- temperatureat reflux for 2.5 h
- filtrationThe reaction mixture was filtered through a pad of Celite®
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-77150eccb119479c8abd2f98a5e68076
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013166B2
Reaction notes
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