HCID 555264, compound → 7-Methoxy-1H-indole
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-])=O)=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][N+]([O-])=O>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:4]=1[NH:14][CH:7]=[CH:6]2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
Compound 3 was synthesized according to the procedure of A. Kalir et al. [supra]. To a 250-mL Parr hydrogenation bottle, 4.893 g of 2 (21.84 mmol) was added. Compound 2 was dissolved in 90 mL of hot ethyl acetate and 9.0 mL of acetic acid. To this solution 0.260 g of 10% palladium on activated carbon (Aldrich) was added. This mixture was hydrogenated overnight at 4 atm. When the pressure stabilized, the reaction mixture was filtered and the solvent removed by rotary evaporation. The residue was dissolved in 60 mL of diethyl ether. The ether solution was washed with 35 mL of 5% aqueous ammonium hydroxide, 5% aqueous hydrochloric acid, and water, dried with MgSO4, and filtered. The ether was removed by rotary evaporation to yield 2.00 g of a green oil. This oil was chromatographed over 85 g of silica gel with 6:1 hexanes:ethyl acetate to yield 1.863 g (58%) of 3 as a very pale yellow oil: 1NMR (CDCl3) δ 3.99 (s, 3H, OCH3), 6.61 (m, 2H), 7.18 (m, 3H), 8.43 (br s, 1H, NH).
Workup
- filtrationthe reaction mixture was filtered
- customthe solvent removed by rotary evaporation
- dissolutionThe residue was dissolved in 60 mL of diethyl ether
- washThe ether solution was washed with 35 mL of 5% aqueous ammonium hydroxide, 5% aqueous hydrochloric acid, and water
- dry with materialdried with MgSO4
- filtrationfiltered
- customThe ether was removed by rotary evaporation
Sources & evidence
- ORD record
- ord-92276ba2d3924e03962945cdb8888d36
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04966913
Reaction notes
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