Morpholine → 2-Morpholino-5-nitrobenzoic acid

HRID 1352268Notes

Reaction equation

HRID 1352268 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>C1COCC1>[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 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12.2 mmol 2-fluoro-5-nitrobenzoic acid (CAS 7304-32-7; commercially available, e.g. from Fluorochem) in 40 ml THF was added 18.2 mmol morpholine and the mixture was stirred at room temperature for 16 h. The volatiles were removed in vacuo and the residue was resuspended in 25 ml water and acidified to pH 4 by dropwise addition of aqueous HCl. The resulting mixture was stirred at room temperature for 30 min, and the resulting crystals were then collected by filtration and dried in vacuo at 50° C. to afford the title compound as a yellow solid (yield 32%). MS (m/e): 251.0 ([M−H]−, 100%)

Workup

  1. customThe volatiles were removed in vacuo
  2. additionacidified to pH 4 by dropwise addition of aqueous HCl
  3. stirringThe resulting mixture was stirred at room temperature for 30 min
  4. filtrationthe resulting crystals were then collected by filtration
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f2790489ec2c4830a1a8e51a1d7b0848
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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