Hydrochloric Acid → HCID 178514928, compound

HRID 232876Notes

Reaction equation

HRID 232876 reaction equation
C[Sn]([N:5]=[N+:6]=[N-:7])(C)C.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:38]=[CH:37][C:24]4[O:25][CH2:26][C:27]5[CH:34]=[C:33]([C:35]#[N:36])[CH:32]=[CH:31][C:28]=5[C:29](=[O:30])[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][CH:10]=1.Cl.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:38]=[CH:37][C:24]4[O:25][CH2:26][C:27]5[CH:34]=[C:33]([C:35]6[NH:36][N:7]=[N:6][N:5]=6)[CH:32]=[CH:31][C:28]=5[C:29](=[O:30])[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 233592232-(7-Chloroquinolin-2-yl)methoxy-8-cyano-11-oxo-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 178514928HCID 178514928, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.03 g of trimethyltin azide was added to 1.07 g of 2-(7-chloroquinolin-2-yl)methoxy-8-cyano-11-oxo-6,11-dihydrodibenz[b,e]oxepine obtained by the same method as in Reference example 34 suspended in 30 ml of xylene and the mixture was refluxed under heating for 13 hours. 1 ml of conc. hydrochloric acid was added to the reaction mixture, the mixture was adjusted to about pH 4 with a 1N-sodium hydroxide aqueous solution and crystals precipitated were collected by filtration. The crystals were dissolved in a chloroform-methanol mixed solution and the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The residue obtained by removing the solvent was applied to silica gel column chromatography to obtain 1.25 g of the title compound.

Workup

  1. customobtained by the same method as in Reference example 34
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 13 hours
  4. customprecipitated
  5. filtrationwere collected by filtration
  6. dissolutionThe crystals were dissolved in a chloroform-methanol mixed solution
  7. washthe organic layer was washed with a saturated saline solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe residue obtained
  10. customby removing the solvent

Sources & evidence

ORD record
ord-03469687d1f84b518df46830a29a8092
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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