Ethanol → HCID 85898789, compound

HRID 1245962Notes

Reaction equation

HRID 1245962 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:20]([N+:21]([O-])=O)=[C:19]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:18]=[C:17]([CH3:31])[C:16]=1[CH3:32].C(O)C>O>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:16]([CH3:32])=[C:17]([CH3:31])[N:18]=[C:19]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:20]=1[NH2:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium Dithionite3×HCID 21913840HCID 21913840, compound

Product 1

HCID 85898789HCID 85898789, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium dithionite (35.13 g, 171.5 mmol), available as approximately 85% pure sodium hydrosulfite, in water (130 mL) was added to a mixture of N-(4-chlorobutyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine (12 g, 34 mmol) and ethanol (340 mL). The mixture was stirred for 1.5 hours. Analysis by thin layer chromatography indicated that the reaction was not complete. Solid sodium dithionite (5 g) was added and the reaction was allowed to stir for an additional 3 hours. The reaction mixture was filtered to remove solids. The filtrate was concentrated under reduced pressure until ˜50 mL of solvent remained. The residue was diluted with dichloromethane (300 mL), washed sequentially with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide 9.5 g of N4-(4-chlorobutyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine as a brown oil.

Workup

  1. stirringto stir for an additional 3 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove solids
  4. concentrationThe filtrate was concentrated under reduced pressure until ˜50 mL of solvent
  5. additionThe residue was diluted with dichloromethane (300 mL)
  6. washwashed sequentially with aqueous sodium bicarbonate, water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3968c8336c34182914c0ba2f18bef37
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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