Ethanol → HCID 59852904, compound

HRID 1670284Notes

Reaction equation

HRID 1670284 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH2:17])=[O:16])=[CH:10][CH:9]=2)=[C:6]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:20]=2[F:28])[CH:5]=[CH:4][N:3]=1.CN(C=O)C.CCO.[NH4+].[Cl-]>[Fe].O>[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH2:17])=[O:16])=[CH:10][CH:9]=2)=[C:6]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=2[F:28])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 59853002HCID 59853002, compound

Product 1

HCID 59852904HCID 59852904, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-(2-amino-4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)phenyl)acetamide (32 mg, 0.086 mmol), DMF (1 mL), EtOH (1 mL) and H2O (1 mL) was treated with Fe powder (67 mg, 1.2 mmol), and NH4Cl (128 mg, 2.4 mmol) and the mixture heated at 100° C. for 20 min. The mixture was filtered through Celite®, the pH of the filtrate adjusted to pH 7 using phosphate buffer and then the mixture was extracted with EtOAc. The organic extract was dried (MgSO4) and concentrated to give the desired product (20 mg, 67%) as a yellow-brown solid. MS (ESI+): m/z 353.32 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5cfa53d57ee45a7873282229d1c210d
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

Loading…