Hydrochloric Acid → HCID 86691457, compound

HRID 1618859Notes

Reaction equation

HRID 1618859 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH:12]([CH3:14])[N:11]([CH3:15])[C:10]2=N)[CH:6]=[CH:7][CH:8]=1.Cl.N([O-])=[O:25].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH:12]([CH3:14])[N:11]([CH3:15])[C:10]2=[O:25])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 86691456HCID 86691456, compound

Product 1

HCID 86691457HCID 86691457, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Product from Step 4 (20 g) was added to 5N hydrochloric acid and the reaction mixture was refluxed under argon purging. To this mixture was added in portions 160 g of sodium nitrite dissolved in water (200 mL). The reaction mixture was refluxed for 30 min further and cooled to 25° C. and extracted with chloroform (2000 mL). The organic layer was dried on anhydrous sodium sulfate, was filtered and then was concentrated under vacuum to obtain dark brown colored crude product of Step 5 (12 g). The crude product was purified on the BIOTAGE® AB ISOLERA™ flash chromatography system as follows: The crude product was dissolved in chloroform (10 mL) and was loaded on a SNAP cartridge containing 340 g silica gel. The column was eluted with a gradient of ethyl acetate and hexane. Fractions containing product were pooled and evaporated under vacuum to obtain viscous yellow oil (21 g). 1H NMR (CDCl3): 1.2 δ (3H, —CH—CH3 of isopropyl), 2.8 δ (3H, —N—(CH3)), 2.2, 3.1, 3.5 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 3.8 δ (3H, —OCH3), 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=296 (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed under argon purging
  2. temperatureThe reaction mixture was refluxed for 30 min further
  3. extractionextracted with chloroform (2000 mL)
  4. dry with materialThe organic layer was dried on anhydrous sodium sulfate
  5. filtrationwas filtered
  6. concentrationwas concentrated under vacuum
  7. customto obtain dark brown colored crude product of Step 5 (12 g)
  8. customThe crude product was purified on the BIOTAGE® AB ISOLERA™ flash chromatography system
  9. dissolutionThe crude product was dissolved in chloroform (10 mL)
  10. additioncontaining 340 g silica gel
  11. washThe column was eluted with a gradient of ethyl acetate and hexane
  12. additionFractions containing product
  13. customevaporated under vacuum

Sources & evidence

ORD record
ord-ff91c9ce84f04a8da9c06c2eb8b2ffc9
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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