Sodium ethoxide → 6-Iodo-4-ethoxy-quinoline-3-carboxylic acid ethyl ester

HRID 1297619Notes

Reaction equation

HRID 1297619 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([I:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[O-:18][CH2:19][CH3:20].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:18][CH2:19][CH3:20])=[CH:13][C:12]([I:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 12052743ethyl 6-iodo-4-chloro-3-quinolinecarboxylate

Product 1

HCID 688284586-Iodo-4-ethoxy-quinoline-3-carboxylic acid ethyl esterYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To the suspension of 4-chloro-6-iodo-quinoline-3-carboxylic acid ethyl ester (example 1c, 1.5 g, 4.1 mmol) in anhydrous ethanol (25 mL) was added sodium ethoxide (0.7 g, 10.3 mol). The mixture was heated to 100° C. under a pressure tube and stirred for 4 h. After cooling to room temperature, the ice water was added. The solid was collected by filtration, washed with water and dried to obtain 6-iodo-4-ethoxy-quinoline-3-carboxylic acid ethyl ester (0.58 g, 38%) as a yellow solid. LC-MS m/e 372 (MH+)

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-af815de7e6e04e0d9ff35307c8039c15
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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