2,5-Pyridinedicarboxylic acid → HCID 53877452, compound

HRID 1200045Notes

Reaction equation

HRID 1200045 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][N:5]=1)([OH:3])=[O:2].C(N([CH2:18][CH3:19])CC)C.Br[CH:21]([O:27][CH2:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[CH2:25]([O:24][C:22]([CH:21]([O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH:21]([C:22]([O:24][CH2:18][CH3:19])=[O:23])[O:27][CH2:28][CH3:29])=[O:11])=[CH:6][N:5]=1)=[O:3])[O:27][CH2:28][CH3:29])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 74932,5-Pyridinedicarboxylic acidHCID 8471TriethylamineHCID 13640440HCID 13640440, compound

Product 1

HCID 53877452HCID 53877452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,5-Dicarboxy-pyridine (1.67 g, 0.01 mol) is suspended in 40 ml of dichloromethane. 2.8 ml of triethylamine are added dropwise, followed by 4.02 g (0.02 mol) of ethyl 2-bromo-2-ethoxy-acetate. The solution is stirred at room temperature for 2 h. After this period, the dichloromethane solution is filtered, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue is purified by silica gel column chromatography (dichloromethane/ethyl acetate) to yield the title compound as a resin; IR (NaCl film): 1730 (CO), 1765 (CO) cm-1.

Workup

  1. waitAfter this period
  2. filtrationthe dichloromethane solution is filtered
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue is purified by silica gel column chromatography (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-98a796c2019a430aa49813d8497f0d7b
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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