Potassium Iodide → 2-Morpholin-4-ylmethyl-6-nitro-benzoic acid methyl ester

HRID 1625120Notes

Reaction equation

HRID 1625120 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13]Br.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 598410552-Morpholin-4-ylmethyl-6-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 4 (3.5 g, crude material), morpholine (0.99 g), potassium carbonate (2.89 g), and potassium iodide (1.66 g) in DMF (22 mL) was stirred at room temperature overnight. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over sodium sulfate, and concentrated to a residue. The crude material was purified by flash chromatography (silica gel, 30-50% ethyl acetate/hexanes) to yield compound 5 as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a residue
  5. customThe crude material was purified by flash chromatography (silica gel, 30-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad7c52b399e6419e8ac889177fc1cc6f
Source dataset
uspto-grants-2014_07
Patent number
US08779131B2

Reaction notes

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