Cesium carbonate → HCID 59813723, compound

HRID 2115814Notes

Reaction equation

HRID 2115814 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=[C:5]2[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH3:35][O:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:36][CH3:37])[N:27]=[CH:26][CH:25]=[C:24]2[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[C:5]2[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 67520306HCID 67520306, compound

Product 1

HCID 59813723HCID 59813723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A resealable tube was charged with methyl 6-hydroxy-4-methyl-1-naphthoate (0.087 g, 0.402 mmol), cesium carbonate (0.393 g, 1.21 mmol), and DMF (2 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at RT for 15 min. 4-Chloro-6,7-dimethoxyquinoline (0.090 g, 0.40 mmol) was added, and the system was again flushed with argon. The tube was sealed and the mixture stirred at 100° C. for 18 h. Additional cesium carbonate (0.393 g, 1.21 mmol) was added and the system was again flushed with argon. The tube was sealed and the mixture stirred at 100° C. for 16 h. The mixture was partitioned between CH2Cl2 and water. The aqueous phase was separated and extracted with CH2Cl2. The aqueous phase was acidified to pH 5-6 with 6 N HCl (aq). The resulting precipitate was filtered and washed with water. The filter cake was dried under vacuum to afford 6-(6,7-dimethoxyquinolin-4-yloxy)-4-methyl-1-naphthoic acid as a light brown solid. MS (ESI, pos. ion) m/z: 390.1 (M+H). Mass Calc'd for C23H19NO5: 389.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. customthe system was again flushed with argon
  4. customThe tube was sealed
  5. stirringthe mixture stirred at 100° C. for 18 h
  6. customthe system was again flushed with argon
  7. customThe tube was sealed
  8. stirringthe mixture stirred at 100° C. for 16 h
  9. customThe mixture was partitioned between CH2Cl2 and water
  10. customThe aqueous phase was separated
  11. extractionextracted with CH2Cl2
  12. filtrationThe resulting precipitate was filtered
  13. washwashed with water
  14. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-96ac1c292aba46328d95f697c16b0857
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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