Cetyl Alcohol → HCID 19864582, compound

HRID 1200044Notes

Reaction equation

HRID 1200044 reaction equation
[C:1]1([C:14]([OH:16])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][N:2]=1.[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>S(Cl)(Cl)=O.N1C=CC=CC=1>[C:1]1([C:14]([O:16][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:12])=[CH:3][N:2]=1

Participants

5

Reactant 2

HCID 2682Cetyl AlcoholHCID 19864568HCID 19864568, compound

Product 1

HCID 19864582HCID 19864582, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Isoquinoline-1,4-dicarboxylic acid (1.8 g, 5 mmol) is refluxed in 10 ml of thionyl chloride for 2 h. The solution is evaporated to dryness and the residue dissolved in 20 ml of dichloromethane. The latter solution is added dropwise to a mixture of 1-hexadecanol (2.90 g, 12 mmol) in 1 ml of pyridine. After 19 h at room temperature, the precipitate is filtered off and the filtrate is evaporated to dryness. The resulting residue is crystallized in toluene/ethanol. The crystals obtained are purified by silica gel flash-column chromatography (dichloromethane). Thus the title compound, m.p. 80.7°-81.4°, is obtained.

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue dissolved in 20 ml of dichloromethane
  3. filtrationthe precipitate is filtered off
  4. customthe filtrate is evaporated to dryness
  5. customThe resulting residue is crystallized in toluene/ethanol
  6. customThe crystals obtained
  7. customare purified by silica gel flash-column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-3d19289a104d44e88e9f980809652f23
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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