7-methoxy-2-(3-nitrobenzylidene)-3,4-dihydro-2H-napthalen-1-one → 3-aminobenzyl-7-methoxy-3,4-dihydro-2H-napthalen-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=3)[C:10]2=[O:13])=[CH:5][CH:4]=1>O1CCCC1.CO.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]1=[O:13]Participants
5
Procedure
A mixture of 626 mg (2.02 mmol) of the product of Example 28 and 125 mg of 10% Pd/C in 15 mL tetrahydrofuran and 15 mL CH3OH was hydrogensted on a Parr (trademark) Hydrogenator under 25 psi H2 at room temperature. After 30 minutes, the reaction mixture was filtered through diatomaceous earth [Celite (trademark)], the filtrate concentrated in vacuo, and the residue purified by silica gel chromatography (5% ethyl acetate-CH2Cl2) to yield 369 mg of pure product, a yellow solid. m.p.: 159°-161° C. MS (LSIMS): 282 M+H, 155 Base; 1H NMR (AC 300, CDCl3): δ3.84 (s, 3H); 3.64 (br s, 2H, NH2); IR (cm31 1): 3360, 6450, 1665. Analysis calculated: C 76.85, H 6.81, N 4.98%; found: C 75.94, H 6.66, N 4.77%.
Workup
- customwas hydrogensted on a Parr (trademark) Hydrogenator under 25 psi H2 at room temperature
- filtrationthe reaction mixture was filtered through diatomaceous earth [Celite (trademark)]
- concentrationthe filtrate concentrated in vacuo
- customthe residue purified by silica gel chromatography (5% ethyl acetate-CH2Cl2)
Sources & evidence
- ORD record
- ord-f0712cff70e9445fb27a009d0e3a6e65
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641789
Reaction notes
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