Diisopropylamine → HCID 53681884, compound

HRID 427521Notes

Reaction equation

HRID 427521 reaction equation
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18]Cl)[CH3:15].C(N[CH:29]([CH3:31])[CH3:30])(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][O:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:21][C:20]1[C:17]([CH3:18])=[CH:16][CH:14]=[CH:15][C:31]=1[CH2:29][CH3:30])=[O:8])[CH3:15]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 183574395-Hydroxy-6-nitropyridine-3-carboxylic acid

Product 1

HCID 53681884HCID 53681884, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

5-hydroxy-6-nitronicotinic acid (1 g, 5 mmol), 2-ethyl-6-methylbenzylchloride (1.85 g, 11 mmol), N,N-diisopropylamine (1.75 g, 14 mmol) and tetrabutylammonium iodide (0.1 g) was added to acetonitrile (10 ml) and was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride and washed with water. The organic layer was separated , dried and evaporated under reduced pressure. Purification of the residue by column chromatograhy on silica gel using n-hexane:methylene chloride (1:1) as eluent gave 0.7 g (29%) of the title compound.

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatograhy on silica gel

Sources & evidence

ORD record
ord-c59e449a55fc4cd4853fe91be4e4215e
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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