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

HRID 221295Notes

Reaction equation

HRID 221295 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-b82a493d4ffe41b897d46b35f42a3629
Source dataset
uspto-grants-2012_06
Patent number
US08207153B2

Reaction notes

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