Ethanol → HCID 22936495, compound

HRID 387803Notes

Reaction equation

HRID 387803 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][CH:16]=[CH:17][C:10]=23)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[NH:15]1[C:11]2=[N:12][CH:13]=[CH:14][C:9]([O:8][C:7]3[CH:18]=[CH:19][C:4]([NH2:1])=[CH:5][CH:6]=3)=[C:10]2[CH:17]=[CH:16]1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22936551HCID 22936551, compound

Product 1

HCID 22936495HCID 22936495, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(4-Nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine (84 mg), iron powder (160 mg), ammonium chloride (320 ml), dimethylformamide (4 ml), ethanol (2 ml) and water (2 ml) were stirred at 100° C. for 15 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added for extraction. The organic layer was washed 5 times with ammonium chloride water and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 230 mg of the target substance as a brown oil.

Workup

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added for extraction
  3. washThe organic layer was washed 5 times with ammonium chloride water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain 230 mg of the target substance as a brown oil

Sources & evidence

ORD record
ord-8c5d824eb85f43a385acdd51f3ecf328
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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