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Cesium carbonate → HCID 68599078, compound

HRID 1185577
Notes
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Reaction equation

HRID 1185577 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][C:9]([CH3:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23]([O:30][C:31](=[O:34])[CH2:32]Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:32][C:31]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:34])[C:12]2[C:7](=[CH:8][C:9]([CH3:16])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 178419010HCID 178419010, compound

Product 1

HCID 68599078HCID 68599078, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228Dimethylformamide
Solvent

Procedure

To a solution of 5.00 g 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid methyl ester in 35 ml of DMF, 8.25 g of cesium carbonate and 5.80 g of Bromo-acetic acid benzyl ester were added and the reaction mixture was stirred for 12 h at RT. Then, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step. Yield: 10.00 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe isolated crude product
  5. customwas pure enough for the next reaction step

Sources & evidence

ORD record
ord-b1a8c09ca04c46c2bb317a98d969544d
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes