Hydrochloric Acid → HCID 22922520, compound

HRID 1081457Notes

Reaction equation

HRID 1081457 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O.C(O)C.[Fe]>[NH2:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[NH:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22922575HCID 22922575, compound

Product 1

HCID 22922520HCID 22922520, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture of 20.75 g of the compound obtained in step A) and 10 g of iron powder in 19 ml of water and 19 ml of ethanol is brought to the reflux point. A solution of 37.5 ml of concentrated hydrochloric acid in 25 ml of water and 25 ml of ethanol is added dropwise to this mixture and reflux is maintained for 1 hour 30 minutes. After cooling, the reaction mixture is poured onto ice and then treated with a saturated solution of NaHCO3 and extracted with AcOEt. The extract is washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (92/8; v/v) as the eluent. 12.71 g of the expected product are obtained after crystallization from isopropyl ether. M.p.=108° C.

Workup

  1. temperaturereflux
  2. temperatureis maintained for 1 hour 30 minutes
  3. temperatureAfter cooling
  4. additionthe reaction mixture is poured onto ice
  5. extractionextracted with AcOEt
  6. washThe extract is washed with water
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off under vacuum
  9. customThe residue is chromatographed on silica using a DCM/MeOH mixture (92/8; v/v) as the eluent

Sources & evidence

ORD record
ord-43256664178d428dbf8bd9d01be11348
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

Loading…