Nitric Acid → 5-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid

HRID 855674Notes

Reaction equation

HRID 855674 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:10]([OH:12])=[O:11]>C(O)(C(F)(F)F)=O>[CH3:5][O:6][C:7]1[C:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:14][C:13]([N+:1]([O-:4])=[O:2])=[C:9]([CH:8]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 216992843-Methoxy-4-(3-morpholinopropoxy)benzoic acid

Product 1

HCID 216992955-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Fuming nitric acid (1.5 ml, 36.2 mmol) was added slowly at 0° C. to a solution of 3-methoxy-4-(3-morpholinopropoxy)benzoic acid (7.78 g, 23.5 mmol) in TFA (25 ml). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 1 hour. The TFA was removed by evaporation and ice was added to the residue. The precipitate was collected by filtration, washed with a minimum of water followed by toluene and ether. The solid was dried under vacuum over phosphorus pentoxide to give 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid (7.54 g) which was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. customThe TFA was removed by evaporation and ice
  3. additionwas added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with a minimum of water
  6. dry with materialThe solid was dried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-d0866e8eddec4d05bfe9a65253a5919a
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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