1-Butanol → HCID 22724072, compound

HRID 333538Notes

Reaction equation

HRID 333538 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1.C(N(CC)CC)C.C(O)CCC>ClCCl>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 7934m-ToluidineHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 22724072HCID 22724072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-chloro-3-nitropyridine (25 g, 158 mmol), m-toluidine (20.5 mL, 189 mmol), triethylamine (26.4 mL, 189 mmol), and 400 mL butanol were added to a 1 L 3-neck round-bottom flask. The reaction mixture was heated overnight under nitrogen. The solvent was evaporated leaving a bright orange solid. The solid was triturated with hexanes and filtered. The filtrate was not pure and contained product, so it was evaporated and purified by column chromatography eluting with 10 and 20% ethyl acetate/hexanes. A total of 3.15 g was obtained from the column. The bulk of the material was dissolved in dichloromethane and washed twice with water, dried over magnesium sulfate, filtered, and evaporated to an orange solid (31.2 g). The total amount obtained was 34.35 g (95%).

Workup

  1. temperatureThe reaction mixture was heated overnight under nitrogen
  2. customThe solvent was evaporated
  3. customleaving a bright orange solid
  4. customThe solid was triturated with hexanes
  5. filtrationfiltered
  6. customso it was evaporated
  7. custompurified by column chromatography
  8. washeluting with 10 and 20% ethyl acetate/hexanes
  9. customA total of 3.15 g was obtained from the column
  10. washwashed twice with water
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated to an orange solid (31.2 g)
  14. customThe total amount obtained

Sources & evidence

ORD record
ord-c3ef1992ae3147509d1c7f4d248b6580
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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