Hydrochloric Acid → HCID 11207166, compound

HRID 1081460Notes

Reaction equation

HRID 1081460 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O.C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:11][CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10730655HCID 10730655, compound

Product 1

HCID 11207166HCID 11207166, compoundYield 37.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 21.5 g of the product obtained in step A) and 13.4 g of iron powder in a mixture of 25 ml of water and 25 ml of ethanol is brought to the reflux point. A solution of 50 ml of concentrated hydrochloric acid in a mixture of 34 ml of water and 34 ml of ethanol is then added slowly. Reflux is maintained for 2 hours. The reaction medium is then poured onto ice, treated with a saturated solution of NaHCO3 and then extracted with DCM, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM as the eluent. 7.2 g of the expected product are obtained after crystallization from heptane. M.p.=62° C.

Workup

  1. additionis then added slowly
  2. temperatureReflux
  3. temperatureis maintained for 2 hours
  4. additionThe reaction medium is then poured onto ice
  5. extractionextracted with DCM
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off under vacuum
  9. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-cc4baecd0d43473aa9e4d7bf39d1da84
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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