Tetrahydrofuran → HCID 21956071, compound

HRID 2246413Notes

Reaction equation

HRID 2246413 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C(OCC)(=O)C.O1CCCC1.C(N(CC)CC)C>CO.[C].[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 219560765-(4-Fluorophenyl)-3-nitropyridin-2-amine

Product 1

HCID 21956071HCID 21956071, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Amino-5-(4-fluorophenyl)-3-nitropyridine (200 mg, 0.86 mmol) was suspended in a mixture of methanol (5 mL), ethyl acetate (5 mL), tetrahydrofuran (5 mL) and triethylamine (2 mL). After addition of 10% palladium carbon (100 mg), the mixture was stirred at room temperature for 1.5 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (C-300, chloroform:methanol=50:1) to give the title compound (76 mg, 44%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (C-300, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-0b6b206e733744b7a06c0e49ed03e770
Source dataset
uspto-grants-2010_03
Patent number
US07687514B2

Reaction notes

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