Dimethylformamide → 4-Methoxy-6-morpholin-4-yl-benzene-1,3-dicarbaldehyde

HRID 349681

Reaction equation

HRID 349681 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.[C:25]([O-])(=[O:27])C.[Na+]>O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:16]([CH:25]=[O:27])=[CH:17][C:18]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 99643354-(3-Methoxyphenyl)morpholine

Product 1

HCID 98347854-Methoxy-6-morpholin-4-yl-benzene-1,3-dicarbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DMF (10 mL) was treated dropwise with phosphorus oxychloride (1.3 g, 14 mmol). The reaction was kept at 25° C. bycooling on ice. The reaction mixture was treated with 4-(3-methoxyphenyl)-morpholine (2.5 g, 13 mmol) in small portions, stirred for 30 min at room temperature, then stirred at 100° C. for 4 h. After cooling, the mixture was poured into aqueous sodium acetate (1 M, 40 mL) and 25 mL of water was added. The resulting precipitate was collected by filtration, washed with water (10 mL), air dried, and purified by flash chromatography (silica gel, 4×15 cm, eluted with 80/20 CHCl3/ether) to yield A and B as white solids: A: (1.0 g, 35%), B: (0.3 g, 9%).

Workup

  1. customwas kept at 25° C. bycooling on ice
  2. stirringstirred at 100° C. for 4 h
  3. temperatureAfter cooling
  4. additionwas added
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water (10 mL), air
  7. customdried
  8. custompurified by flash chromatography (silica gel, 4×15 cm, eluted with 80/20 CHCl3/ether)
  9. customto yield A and B as white solids

Sources & evidence

ORD record
ord-53f2f464dfaf4ecc9d38a5559f4208bb
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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