Water → HCID 86626289, compound

HRID 1097574Notes

Reaction equation

HRID 1097574 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=1.C(N(CC)CC)C.[CH2:21](N)[CH:22]([CH3:24])[CH3:23].O>CN(C=O)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 86626289HCID 86626289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A modification of the method described in Part A of Example 4 was used to treat 2,4-dichloro-5,6-dimethyl-3-nitropyridine (Dellaria et al, U.S. Pat. No. 6,545,016, Example 7, Part A, 50.0 g, 0.194 mol) with triethylamine (47 mL, 0.34 mol) and isobutylamine (27 mL, 0.27 mol) in anhydrous DMF (500 mL). The work-up procedure was as follows. The reaction mixture was poured into hot water (1 L). The resulting mixture was extracted with chloroform (2×800 mL), and the combined extracts were dried over magnesium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure to provide 60.78 g of 2-chloro-5,6-dimethyl-4-(2-methylpropyl)-3-nitropyridine as a bright orange solid.

Workup

  1. extractionThe resulting mixture was extracted with chloroform (2×800 mL)
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered through a layer of CELITE filter agent
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c79855a20614917a8a0b5621bc60d14
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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