Sodium Iodide → 5-Methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehyde

HRID 1821425Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:13]([O:14][CH3:15])=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[I-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:15][O:14][C:13]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:7][C:8]([N+:16]([O-:18])=[O:17])=[C:9]([CH:12]=1)[CH:10]=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(3-Chloropropyloxy)-5-methoxy-2-nitrobenzaldehyde (0.40 g, 1.5 mmol) was dissolved in toluene (6.0 mL) and the solution was added with potassium carbonate (1.0 g, 7.3 mmol) dissolved in morpholine (0.38 mL, 4.4 mmol), sodium iodide (0.44 g, 2.9 mmol), tetrabutylammonium bromide (24 mg, 0.007 mmol) and water (2.0 mL), followed by stirring at 100° C. for 19 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100) and concentrated to obtain 5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehyde (0.26 g, 54%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100)
concentrationconcentrated

Sources & evidence

ORD record: ord-85a5bf4bc6f04f29b8200ec1b4f667b3
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605272B2

Reaction notes

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