Water → HCID 23157388, compound

HRID 507928Notes

Reaction equation

HRID 507928 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15].O>N1C=CC=CC=1>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1)(=[O:25])=[O:24])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 155402-Nitrobenzenesulfonyl chlorideHCID 23157625HCID 23157625, compound

Product 1

HCID 23157388HCID 23157388, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 3-(6-aminopyridin-3-yl)propanoate (500 mg, 2.78 mmol) in pyridine (5 mL) was added 2-nitrobenzenesulfonyl chloride (924 mg, 4.17 mmol), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give the title compound (365 mg, yield 36%) as yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-75a2d763dab14e1484093ea42436dda7
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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