Hydrochloric Acid → HCID 58153430, compound

HRID 1894641Notes

Reaction equation

HRID 1894641 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[N:4][C:5]([CH3:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.Cl.ClCCl.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:11])=[N:4][C:3]=1[O:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 58153476HCID 58153476, compound

Product 1

HCID 58153430HCID 58153430, compoundYield 131.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50 ml single-necked round-bottomed flask equipped with a condensor, 1.36 g of crude 3-bromo-6-methyl-2-(4-methyl-pentyloxy)-5-nitro-pyridine is dissolved in 3.15 ml of methanol and the resulting solution stirred. Under cooling using an ice/water bath, 3.15 ml of concentrated aqueous HCl is added dropwise by syringe (precipitation is observed). The ice bath is removed and 2.23 g anhydrous SnCl2 is added in portions. Stirring is continued under heating to reflux for 5.5 h (yellow suspension). After cooling this mixture to ambient temperature, it is concentrated in vacuo to give a yellow solid. After adding dichloromethane, 10 ml of a 4 M aqueous NaOH solution is added (pH 12). After extraction, the organic phase is dried over Na2SO4, filtered and the solvent removed in vacuo to give 1.62 g of a yellow oil. Purification is done by flash chromatography [silica gel cartridge (50 g, 150 ml) of a solid deposition with heptane/ethyl acetate 4:1 (v:v)] to give 490 mg of the compound in the form of a yellow oil. RP HPLC: Retention time of compound: 2.12 minutes.

Workup

  1. temperatureUnder cooling
  2. custom(precipitation is observed)
  3. customThe ice bath is removed
  4. addition2.23 g anhydrous SnCl2 is added in portions
  5. stirringStirring
  6. temperatureunder heating
  7. temperatureto reflux for 5.5 h (yellow suspension)
  8. concentrationit is concentrated in vacuo
  9. customto give a yellow solid
  10. additionis added (pH 12)
  11. extractionAfter extraction
  12. dry with materialthe organic phase is dried over Na2SO4
  13. filtrationfiltered
  14. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d71ac0ff63584f41a528ddd611ffb00b
Source dataset
uspto-grants-2013_08
Patent number
US08513286B2

Reaction notes

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