Tetrabutylammonium Fluoride → HCID 19592391, compound

HRID 613540Notes

Reaction equation

HRID 613540 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:29]2[C:24](=[C:25]([NH:30][C:31](=[O:40])[C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[CH2:41][O:42][CH3:43])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:39][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]([Cl:38])[C:32]=1[C:31]([NH:30][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[N:23]=[CH:22][C:21]([CH2:41][O:42][CH3:43])=[C:20]2[CH2:19][OH:18])=[O:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19592678HCID 19592678, compound

Product 1

HCID 19592391HCID 19592391, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(tert-butyldiphenylsilyloxymethyl)-8-(2,6-dichlorobenzoylamino)-3-(methoxymethyl)quinoline (359 mg) in tetrahydrofuran was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.684 ml) at ambient temperature, and the mixture was stirred for 1 hour at the same temperature. The mixture was partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from isopropyl alcohol to give 8-(2,6-dichlorobenzoylamino)-4-hydroxymethyl-3-(methoxymethyl)quinoline (186 mg).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-97aa1accab6e4944842e7f96ecf8d604
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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