Dicyclohexylcarbodiimide → 2-Allyloxy-1-methylethyl 5-chloroquinolin-8-oxyacetate

HRID 1769263

Reaction equation

HRID 1769263 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:17]([O:20][CH2:21][CH:22]([CH3:24])O)[CH:18]=[CH2:19].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=NC=CC=1)C>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16][CH:22]([CH3:24])[CH2:21][O:20][CH2:17][CH:18]=[CH2:19])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1233783-Pyridinamine, N,N-dimethyl-HCID 5421782-Propanol, 1-(2-propenyloxy)-HCID 15257197Cloquintocet

Product 1

HCID 154841292-Allyloxy-1-methylethyl 5-chloroquinolin-8-oxyacetateYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5.0 g (0.021 mol) of 5-chloroquinolin-8-oxyacetic acid and 2.44 g (0.021 mol) of 2-allyloxy-1-methylethanol are suspended in a mixture of 40 ml of methylene chloride and 40 ml of dimethylformamide and the suspension is cooled to 0° C. 4.78 g (0.023 mol) of dicyclohexylcarbodiimide, dissolved in 10 ml of methylene chloride, are added dropwise at this temperature, and 200 mg of 3-(N,N-dimethylamino)-pyridine are then added. The mixture is stirred at room temperature for 15 hours and the precipitate which has separated out is filtered off with suction and rinsed with 50 ml of methylene chloride. The filtrate is washed with 100 ml of 0.5 N HCl, with 100 ml of potassium bicarbonate solution and with 3 portions of in each case 50 ml of water. The organic phase is dried over magnesium sulfate and the solvent is stripped off in vacuo. The residue is recrystallized from n-heptane. 5.1 g (72.4% of theory) of 2-allyloxy-1-methylethyl 5-chloroquinolin-8-oxyacetate of melting point 59° C. are obtained in this manner.

Workup

  1. additionare then added
  2. customthe precipitate which has separated out
  3. filtrationis filtered off with suction
  4. washrinsed with 50 ml of methylene chloride
  5. washThe filtrate is washed with 100 ml of 0.5 N HCl, with 100 ml of potassium bicarbonate solution and with 3 portions of in each case 50 ml of water
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customThe residue is recrystallized from n-heptane

Sources & evidence

ORD record
ord-df1b135afad3466692a98882f3761cf4
Source dataset
uspto-grants-1995_01
Patent number
US05380852

Linked notes

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