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

HRID 1821425
Notes
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Reaction equation

HRID 1821425 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 866282194-(3-Chloropropyloxy)-5-methoxy-2-nitrobenzaldehyde

Product 1

HCID 866282185-Methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehydeYield 54%

Reagents, catalysts & solvents 3

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100)
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes