Ethanol → HCID 85898813, compound

HRID 1352622Notes

Reaction equation

HRID 1352622 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1[C:22]([N+:23]([O-])=O)=[C:21]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:20]=[C:19]([CH3:33])[C:18]=1[CH3:34].C(O)C.O1CCCC1>O>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1[C:18]([CH3:34])=[C:19]([CH3:33])[N:20]=[C:21]([O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:22]=1[NH2:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium Dithionite2×HCID 21913479HCID 21913479, compound

Product 1

HCID 85898813HCID 85898813, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium dithionite (24.01 g, 137.9 mmol) in water (90 mL) was added to a mixture of N-(6-chlorohexyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine (10.42 g, 27.58 mmol) and ethanol (276 mL). After about 4 hours sodium dithionite (6.71 g) in water (20 mL) was added to the reaction mixture. About 1 hour later tetrahydrofuran (100 mL) was added. When analysis by thin layer chromatography indicated that the reaction was complete, the reaction mixture was filtered to remove solids. The solids were rinsed with ethanol. The rinses and the filtrate were concentrated under reduced pressure. The residue was diluted with toluene (200 mL) and then concentrated under reduced pressure to remove the bulk of the solvent. The residue was partitioned between ethyl acetate (200 mL) and water (50 mL). The aqueous layer was separated, combined with saturated aqueous sodium bicarbonate to adjust to pH 8 and then extracted with ethyl acetate. The combined organics were washed with brine (100 mL), dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was combined with toluene and then concentrated under reduced pressure to provide 12.12 g of N4-(6-chlorohexyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove solids
  3. washThe solids were rinsed with ethanol
  4. concentrationThe rinses and the filtrate were concentrated under reduced pressure
  5. additionThe residue was diluted with toluene (200 mL)
  6. concentrationconcentrated under reduced pressure
  7. customto remove the bulk of the solvent
  8. customThe residue was partitioned between ethyl acetate (200 mL) and water (50 mL)
  9. customThe aqueous layer was separated
  10. extractionextracted with ethyl acetate
  11. washThe combined organics were washed with brine (100 mL)
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-520019a9871f4e699b5735ba6b21418c
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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