Dimethylformamide → HCID 178472636, compound

HRID 66142Notes

Reaction equation

HRID 66142 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:11][C:10]2[CH:12]=[CH:13][C:14](=[O:18])[C:15]([OH:17])=[CH:16][C:9]=2[C:8](=[O:19])[CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].CN(C)C=O.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][N:11]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][C:8](=[O:19])[C:9]2[CH:16]=[C:15]([OH:17])[C:14](=[O:18])[CH:13]=[CH:12][C:10]1=2)[CH3:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178469293HCID 178469293, compound

Product 1

HCID 178472636HCID 178472636, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,7-Dihydro-4,7-dioxo-6-hydroxy-1H-cyclohepta[b]pyridine-2-carboxylic acid ethyl ester (12.0 g, described in Example 3) is added to a stirring mixture of sodium hydride (57%, 2.8 g) and dimethylformamide (400 ml) at room temperature. Ethyl bromoacetate (15.8 g) is added. The mixture is stirred at room temperature for 20 hr and poured on ice. Water is added and the mixture is extracted with chloroform. The organic extract is dried over sodium sulfate and evaporated. The residue is crystallized from ethyl acetate to give the title compound, mp 186°-188° C.

Workup

  1. additionpoured on ice
  2. extractionthe mixture is extracted with chloroform
  3. extractionThe organic extract
  4. dry with materialis dried over sodium sulfate
  5. customevaporated
  6. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2fd992347d004f68bf597af9af29ffdb
Source dataset
uspto-grants-1978_12
Patent number
US04130649

Reaction notes

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