tert-Butanol → HCID 13433721, compound

HRID 2189461Notes

Reaction equation

HRID 2189461 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[C:12](O)([CH3:15])([CH3:14])[CH3:13].[I-].ClC1C=CC=C[N+]=1C.C(N(CCCC)CCCC)CCC>ClCCl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([O:10][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:9]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 4338043,6-Dichloropyridazine-4-carboxylic acid

Product 1

HCID 13433721HCID 13433721, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,6-dichloropyridazine-4-carboxylic acid (5.79 g, 30 mmol), tert-butanol (2.45 g, 33 mmol), 2-chloro-1-methylpyridinium iodide (6.12 g, 24 mmol), and tributylamine (8.9 g, 48 mmol) in dichloromethane (52 mL) was stirred at refluxing under N2 for 3 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified using a silica gel cartridge (330 g) which was pretreated with 1% Et3N in hexanes for 10 min at 10 mL/min, eluting with a gradient of EtOAc (0-50%) in hexanes to afford 6.1 g (81%) of the title compound as a white solid. HPLC/MS (Method B): retention time=2.95 min, [M+H]+=249.1.

Workup

  1. temperatureat refluxing under N2 for 3 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified
  4. washeluting with a gradient of EtOAc (0-50%) in hexanes

Sources & evidence

ORD record
ord-7172713f2da945aea2a965e8fe0495f2
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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