Pyridine → HCID 67392996, compound

HRID 913349Notes

Reaction equation

HRID 913349 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[C:14]([NH:19][C:20](=O)[CH2:21][CH2:22][CH3:23])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].N1C=CC=CC=1>CCCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:27][C:20]([CH2:21][CH2:22][CH3:23])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 178454479HCID 178454479, compound

Product 1

HCID 67392996HCID 67392996, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A mixture of the N-(7-benzyloxy-4-hydroxyquinolin-3-yl)butyramide prepared in Part E (2.97 g, 8.83 mmol), P2S5 (1.96 g, 4.41 mmol), and pyridine was placed under a nitrogen atmosphere and heated to reflux. The resulting solution was cooled and the excess P2S5 was quenched slowly with 10% aqueous Na2CO3 (10 mL). The reaction mixture was partitioned between water (40 mL) and CH2Cl2 (100 mL). The organic layer was washed with 0.1 M aqueous HCl (50 mL), dried over MgSO4, filtered and concentrated to yield a brownish-yellow solid. The solid was treated with boiling heptane (40 mL) and filtered. The filtrate was allowed to cool and a solid formed. The light yellow solid was isolated by filtration and washed with cold heptane to provide 7-benzyloxy-2-propylthiazolo[4,5-c]quinoline (1.74 g, 59%).

Workup

  1. temperatureheated to reflux
  2. temperatureThe resulting solution was cooled
  3. customthe excess P2S5 was quenched slowly with 10% aqueous Na2CO3 (10 mL)
  4. customThe reaction mixture was partitioned between water (40 mL) and CH2Cl2 (100 mL)
  5. washThe organic layer was washed with 0.1 M aqueous HCl (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a brownish-yellow solid
  10. filtrationfiltered
  11. temperatureto cool
  12. customa solid formed
  13. customThe light yellow solid was isolated by filtration
  14. washwashed with cold heptane

Sources & evidence

ORD record
ord-4dccd69182984798816693ed474af020
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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