3''-Fluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine → 3''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine

HRID 2264179Notes

Reaction equation

HRID 2264179 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([N+:14]([O-])=O)[CH:13]=1>[Pd].C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([NH2:14])[CH:13]=1

Participants

4

Reactant 1

HCID 595960063''-Fluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine

Product 1

HCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A suspension of 3″-fluoro-5′-nitro-3,2′:3′,4″-terpyridin-6′-amine (2.25 g, 7.23 mmol) and 10% palladium on carbon (0.4 g) in a mixture of THF/ethanol 40:60 (100 mL) was stirred under hydrogen atmosphere. After 3 h, the mixture was filtered through Celite® and the filter cake was washed with ethanol. The combined filtrate and washings were evaporated to give the title compound as a solid (2.01 g, 99%).

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. washthe filter cake was washed with ethanol
  3. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-898427f72191472aa74b76c1c5f1fb0f
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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