Nitric Acid → Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate

HRID 2213859Notes

Reaction equation

HRID 2213859 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>ClCCl.C(O)(=O)C.O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:20]([N+:6]([O-:9])=[O:7])=[CH:21][C:22]=1[O:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 21958890HCID 21958890, compound

Product 1

HCID 11773033Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoateYield 161.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated sulphuric acid (110 ml) and concentrated nitric acid (19.0 ml, 0.289 mol) were added cautiously, over a 50 minute period, to a two-phase system containing a stirred solution of ethyl 3-methoxy-4-(3-morpholinopropoxy)benzoate (76.5 g, 0.237 mol) in dichloromethane (600 ml), acetic acid (300 ml) and water (70 ml) at 5° C. The reaction was allowed to warm to ambient temperature over 18 hours, the aqueous phase was separated, and the aqueous phase was taken to pH 9 by addition of 40% aqueous sodium hydroxide solution (775 ml). Extraction of the aqueous phase with dichloromethane (3×600 ml) and subsequent solvent evaporation in vacuo yielded ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate (141.3 g, 86% yield) as a yellow gum:

Workup

  1. customthe aqueous phase was separated
  2. additionthe aqueous phase was taken to pH 9 by addition of 40% aqueous sodium hydroxide solution (775 ml)
  3. extractionExtraction of the aqueous phase
  4. customwith dichloromethane (3×600 ml) and subsequent solvent evaporation in vacuo

Sources & evidence

ORD record
ord-b9c40cfb6f7b4982b314a98000b39a72
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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