Water → HCID 70250426, compound

HRID 2265093Notes

Reaction equation

HRID 2265093 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH3:16])=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].O.O1CCCC1>[Fe].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[CH3:16])=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 11031413HCID 11031413, compound

Product 1

HCID 70250426HCID 70250426, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Compound 6a (31.7 g), iron powder (41.1 g), ammonium chloride (18.1 g), and water (173 ml) were added to a mixed solution of tetrahydrofuran (280 ml) and methanol (280 ml) in a nitrogen atmosphere. The mixture was stirred at 70° C. for 1 hour. After the reaction mixture was allowed to cool, and filtered, the filtrate was separated with ethyl acetate and water. The organic layer was washed once with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and as a result, Compound 6b (25.7 g, 94%) was obtained as an orange solid.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customthe filtrate was separated with ethyl acetate and water
  4. washThe organic layer was washed once with water and once with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4c592b0d722c4a6a805b4192174c21a1
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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