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

HRID 1597210Notes

Reaction equation

HRID 1597210 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:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[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 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 216992843-Methoxy-4-(3-morpholinopropoxy)benzoic acid

Product 1

HCID 694655255-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzoic acid trifluoroacetate

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 evaporated and ice was added to the residue. The precipitate was collected by filtration and 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 trifluoroacetate (7.54 g, 71%yield) which was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. customThe TFA was evaporated
  3. additionice was 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-da5c8e1c14474ac6bd6156bfbbdeb9ff
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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