Tetrabutylammonium Fluoride → HCID 13200299, compound

HRID 1903221Notes

Reaction equation

HRID 1903221 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si](C)(C)CCOC([NH:26][C@@H:27]1[CH2:29][C@H:28]1[S:30][C:31]1[C:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1)=O>O1CCCC1.C(#N)C>[NH2:26][C@@H:27]1[CH2:29][C@H:28]1[S:30][C:31]1[C:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54031289HCID 54031289, compound

Product 1

HCID 13200299HCID 13200299, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1 M-solution of tetra-n-butylammonium fluoride in tetrahydrofuran (12 ml.) was added to a solution of 2-{trans-2-[2-(trimethylsilyl)ethoxycarbonylamino]-cyclopropylthio}-3-phenylquinoline (3.5 g.) in dry acetonitrile (35 ml.), and the mixture was stirred at 50° under argon for 5 hr. The mixture was cooled, the solvent was evaporated, and the residual oil was partitioned between ethyl acetate (70 ml.) and water (35 ml.). The mixture was separated and the organic phase was washed with water (2×30 ml.) and dried (Na2SO4). The solvent was evaporated and the residual brown oil (2.7 g.) was chromatographed on basic alumina (180 gm., Brockmann, Grade III) eluted with 30% v/v chloroform in petroleum ether to give 2-(trans-2-aminocyclopropylthio)-3-phenylquinoline as a pale yellow oil, which gave a hydrochloride of m.p. 140°.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated
  3. customthe residual oil was partitioned between ethyl acetate (70 ml.) and water (35 ml.)
  4. customThe mixture was separated
  5. washthe organic phase was washed with water (2×30 ml.)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated
  8. customthe residual brown oil (2.7 g.) was chromatographed on basic alumina (180 gm., Brockmann, Grade III)
  9. washeluted with 30% v/v chloroform in petroleum ether

Sources & evidence

ORD record
ord-25f046e28c1f4dad9766585c7a5b37db
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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