Potassium Carbonate → HCID 85898799, compound

HRID 1008074Notes

Reaction equation

HRID 1008074 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[C:11]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=[C:9]([CH3:23])[C:8]=1[CH3:24].[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CCCCCCCC)=CC=2)=CC=1)CCCCCCC.C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.ClCCl>[Cl:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:8]([CH3:24])=[C:9]([CH3:23])[N:10]=[C:11]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]=1[NH2:13]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 24489Sodium DithioniteHCID 374511,1'-Dioctyl-4,4'-bipyridin-1-ium dibromideHCID 21913155HCID 21913155, compound

Product 1

HCID 85898799HCID 85898799, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(3-chloropropyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine hydrochloride (12.62 g, 33.72 mmol), 1,1′-di-n-octyl-4,4′-bipyridinium dibromide (dioctyl viologen) (910 mg, 1.69 mmol), dichloromethane (227 mL), water (28 mL) and potassium carbonate (2.33 g, 16.9 mmol) were added sequentially to a 1 L round bottom flask. The reaction mixture was allowed to stir under nitrogen. A solution of of potassium carbonate (23.30 g, 168.6 mmol) and sodium dithionite (26.42 g, 174.1 mmol) in water (114 mL) was added to the reaction mixture. The reaction mixture was heated at reflux for about 2.5 hr and then allowed to cool to ambient temperature. The layers were separated. The aqueous layer was extracted with dichloromethane (100 mL). The combined organics were dried over sodium sulfate, filtered and then concentrated under reduced pressure to provide N4-(3-chloropropyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine as a brown sludge. This material was used directly in the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about 2.5 hr
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (100 mL)
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a44fccf98c64f7db5a9e7d2aeca46fa
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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