Hydrochloric Acid → 4-Dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzene

HRID 2075434Notes

Reaction equation

HRID 2075434 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14](C=O)=[CH:13][C:12]=2[N+:19]([O-:21])=[O:20])[CH2:4][CH2:3]1.[CH:22]([O:27][CH3:28])([O:25][CH3:26])OC.Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[CH3:28][O:27][CH:22]([O:25][CH3:26])[C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][O:2][CH2:7][CH2:6]2)=[C:12]([N+:19]([O-:21])=[O:20])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 231179204-(2-Morpholinoethoxy)-3-nitrobenzaldehyde hydrochloride

Product 1

HCID 231179024-Dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzeneYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-morpholinoethoxy)-3-nitrobenzaldehyde hydrochloride obtained in Step 1 (2.97 g, 9.38 mmol) in dichloromethane (10.0 mL) was added with trimethyl orthoformate (15.0 mL, 13.7 mmol) and a 10% solution of hydrogen chloride in methanol (5.00 mL), followed by stirring at room temperature for 4 hours. The reaction mixture was added with potassium carbonate (10.0 g, 72.4 mmol), then stirred at room temperature for 5 hours, and the solvent was evaporated under reduced pressure. The residue was added with water (50 mL) and was extracted with ethyl acetate (50 mL×3). After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain 4-dimethoxymethyl-1-(2-morpholinoethoxy)-2-nitrobenzene (2.98 g, 97%).

Workup

  1. stirringstirred at room temperature for 5 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with water (50 mL)
  4. extractionwas extracted with ethyl acetate (50 mL×3)
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a26484fe7ab416a8aaea2f238edf426
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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