Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate → HCID 178469656, compound

HRID 1841526Notes

Reaction equation

HRID 1841526 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:24]=[CH:23][C:9]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([I:25])[CH:7]=1)(=[O:3])[CH3:2]>O(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:24]=[C:23]2[C:9](=[C:8]([I:25])[CH:7]=1)[N:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]2[OH:20])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 22724556Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate

Product 1

HCID 178469656HCID 178469656, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate (1.75 g) in Ph2O (20 mL) is heated at 250° C. for 40 min. The reaction is cooled to room temperature and diluted with hexanes. The resulting solid is collected and dried. The crude solid is adsorbed onto silica and chromatographed (Biotage flash 40S, gradient from CH2Cl2 to 2% MeOH/CH2Cl2). Product containing fractions are combined and concentrated to yield 0.98 g (62%) of ethyl 6-[(acetyloxy)methyl]-4-hydroxy-8-iodo-3-quinolinecarboxylate, m.p. 119-123° C.

Workup

  1. customThe resulting solid is collected
  2. customdried
  3. customchromatographed (Biotage flash 40S, gradient from CH2Cl2 to 2% MeOH/CH2Cl2)
  4. additionProduct containing fractions
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c42c9579730492294b0f84fe6defa9d
Source dataset
uspto-grants-2004_01
Patent number
US06683181B2

Reaction notes

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