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

HRID 1746291Notes

Reaction equation

HRID 1746291 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-9207f58613fb440bb20887cd3395a3a9
Source dataset
uspto-grants-2015_10
Patent number
US09149477B2

Reaction notes

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