Cesium carbonate → HCID 24823892, compound

HRID 2115799Notes

Reaction equation

HRID 2115799 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=[CH:11]2.[CH3:21][NH:22][C:23](=[O:31])[C:24]1[CH:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1>CS(C)=O>[CH3:21][NH:22][C:23]([C:24]1[CH:29]=[C:28]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=[CH:11]3)[CH:27]=[CH:26][N:25]=1)=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 24823892HCID 24823892, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (52.0 g, 160 mmol) was added to a solution of 6-hydroxy-1-naphthoic acid (10 g, 53.0 mmol) in DMSO (140 mL). After stirring vigorously for 15 min N-methyl-4-chloropicolinamide (10.8 g, 61.0 mmol) was introduced and the mixture was heated at 100° C. for 10 h. After cooling to RT, the mixture was filtered through a plug of silica gel (10:1:0.5; CH2Cl2,CH3OH, AcOH). The filtrate was concentrated and triturated with EtOAc to provide the title compound as a slightly pink solid. MS (ESI, pos. ion) m/z: 323.3 (M+1). Mass Calc'd for C18H12N2O4: 322.31.

Workup

  1. additionwas introduced
  2. temperatureAfter cooling to RT
  3. filtrationthe mixture was filtered through a plug of silica gel (10:1:0.5; CH2Cl2,CH3OH, AcOH)
  4. concentrationThe filtrate was concentrated
  5. customtriturated with EtOAc

Sources & evidence

ORD record
ord-36bf50cc36884e0a95389aafa9fbf679
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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