Sodium Methoxide → 6-Iodo-4-methoxy-quinoline-3-carboxylic acid methyl ester

HRID 1297607Notes

Reaction equation

HRID 1297607 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])C.[CH3:18][O-:19].[Na+]>CO>[CH3:1][O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:19][CH3:18])=[CH:13][C:12]([I:17])=[CH:11][CH:10]=2)=[O:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12052743ethyl 6-iodo-4-chloro-3-quinolinecarboxylate

Product 1

HCID 688283896-Iodo-4-methoxy-quinoline-3-carboxylic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To the suspension of 4-chloro-6-iodo-quinoline-3-carboxylic acid ethyl ester (14 g, 0.039 mol) in anhydrous methanol (180 mL) was added sodium methoxide (4.16 g, 0.07 mol). The mixture was heated to 100° C. under a pressure tube and stirred for 10 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-methoxy-quinoline-3-carboxylic acid methyl ester (12 g, 92%) as a yellow solid. LC-MS m/e 344 (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-ee543b9edbfe424e84d96297ae749d0a
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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