Cesium carbonate → HCID 59813238, compound

HRID 1925303Notes

Reaction equation

HRID 1925303 reaction equation
[OH: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]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][C:23]=1[C:36]#[N:37]>CN(C)C=O>[C:36]([C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:22]=1[O:1][C:2]1[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]3)=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)#[N:37]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 54638006-Hydroxy-1-naphthoic acidHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 59813238HCID 59813238, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A resealable tube was charged with 6-hydroxy-1-naphthoic acid (0.596 g, 3.17 mmol), cesium carbonate (3.10 g, 9.51 mmol), and N,N-dimethylformamide (15 mL, Aldrich). The system was flushed with argon, the tube was sealed, and the mixture stirred at RT for 15 min. A solution of 4-chloro-3-cyano-6,7-dimethoxyquinoline (0.788 g, 3.17 mmol) in N,N-dimethylformamide (10 mL) was added (along with a 5 mL DMF rinse), and the system was again flushed with argon. The tube was sealed and the mixture stirred at 60° C. for 2 h. The mixture was diluted with water (30 mL) and 6 N HCl (aq) was added dropwise with stirring until the pH of the solution was 6-7. The resulting precipitate was filtered and washed with water. The filter cake was dried under vacuum to afford 6-(3-cyano-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid as a light brown solid. MS (ESI, pos. ion) m/z: 401.0 (M+H). Mass Calc'd for C23H16N2O5: 400.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. washrinse), and the system
  4. customwas again flushed with argon
  5. customThe tube was sealed
  6. stirringthe mixture stirred at 60° C. for 2 h
  7. additionThe mixture was diluted with water (30 mL) and 6 N HCl (aq)
  8. additionwas added dropwise
  9. stirringwith stirring until the pH of the solution
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water
  12. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-843b5336db614a09a2140bdbe18a2d58
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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