Morpholine → 2-Morpholino-5-nitrobenzoic acid

HRID 2223486Notes

Reaction equation

HRID 2223486 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCOCC1>[N:14]1([C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 27257552-Morpholino-5-nitrobenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzoic acid (4.86 g, 26.2 mmol) in dioxane (50 ml) was added morpholine (11.5 mL). The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo. The residue was dissolved in water, and the mixture was acidified with HCl 2N. The solid was filtered, washed with water and dried to provide the title compound (6.2 g, 93%) as a yellow solid, MS (m/e): 251.2 (MH−, 100%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-293a4f1ece224df691e680d33ac56081
Source dataset
uspto-grants-2008_05
Patent number
US07375226B2

Reaction notes

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