Hydrochloric Acid → HCID 25072939, compound

HRID 1035679Notes

Reaction equation

HRID 1035679 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[O:25].Cl.[NH+]1C=CC=CC=1.Cl>>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[O:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21584435Pyridinium hydrochlorideHCID 59443489HCID 59443489, compound

Product 1

HCID 25072939HCID 25072939, compoundYield 42%

Procedure

The compound was prepared by refluxing 3-(2-methoxy-6-(3-methoxyphenyl)-naphthalene-1-yl)-N-(methylsulfonyl)benzamide (80 mg, 0.17 mmol, 1 eq) with pyridinium hydrochloride (302 mg, 15 eq) for two hours. After cooling, 2 ml of 1 N HCl was added, and the water phase was extracted with ethyl acetate. The organic phase was dried and concentrated in vacuum. After purification by column chromatography with 10% methanol in dichloromethane, the desired compound was obtained in 42% yield, 31 mg.

Workup

  1. customThe compound was prepared
  2. temperatureAfter cooling
  3. extractionthe water phase was extracted with ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuum
  6. customAfter purification by column chromatography with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-bb8fd5e9da10460f8de15fd41f3488a9
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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