1,1-Dimethyl-5-nitro-3-phenyl-1H-indene → 5-Amino-1,1-dimethyl-3-phenyl-1H-indene
Reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3]1>C1C=CC=CC=1.O.C(OCC)(=O)C.[Fe]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2]([CH3:20])([CH3:1])[CH:3]=[C:4]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Procedure
To a mixture of 1,1-dimethyl-5-nitro-3-phenyl-1H-indene (0.56 g, 2.11 mmol) in 5 mL of benzene was added 33% ferric chloride (1 mL) and 4 mL of water. The mixture was stirred at reflux and iron powder 1.00 g, 5.28 mmol) was added in four portions during 2 hours. The resulting mixture was stirred at reflux for additional 18 hours. The mixture was diluted with 20 mL of water and 20 mL of ethyl acetate, and filtered through a pad of celite. The filtrate was extracted with ethyl acetate (20 mL×3). The combined extracts were dried over magnesium sulfate to give 0.49 g (98% yield) of the crude title compound which was not further purified and used in the next reaction; 1H-NMR (CDCl3) δ1.37 (s, 6H), 6.40 (s, 1H), 6.71 (dd, J=2.0, 7.9 Hz, 1H), 6.93 (d, J=2.0 Hz, 1H), 7.19 (d, J=7.9 Hz, 1H), 7.36-7.58 (m, 5H); MS m/e 236 (MH+).
Workup
- temperatureat reflux
- stirringThe resulting mixture was stirred
- temperatureat reflux for additional 18 hours
- filtrationfiltered through a pad of celite
- extractionThe filtrate was extracted with ethyl acetate (20 mL×3)
- dry with materialThe combined extracts were dried over magnesium sulfate
Sources & evidence
- ORD record
- ord-78e73369782a4cabb3f41a0653a2f175
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05618839
Reaction notes
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