Tetrabutylammonium Fluoride → N1-(4-Methoxybenzoyl)-N2-(4-propylbenzoyl)-4-hydroxy-1,2-benzenediamine

HRID 427576Notes

Reaction equation

HRID 427576 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:24][C:25](=[O:35])[C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH3:34])=[CH:28][CH:27]=3)=[CH:12][C:13]([O:16][Si](C(C)(C)C)(C)C)=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:24][C:25](=[O:35])[C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH3:34])=[CH:28][CH:27]=3)=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)=[O:8])=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54350608N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Product 1

HCID 21352799N1-(4-Methoxybenzoyl)-N2-(4-propylbenzoyl)-4-hydroxy-1,2-benzenediamineYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine (360 mg, 0.69 mmol) in tetrahydrofuran (20 mL) cooled to 0° C. was added a 1 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1.4 mL, 1.4 mmol). After 15 min, the reaction mixture was diluted with water and partitioned with ethyl acetate. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 10% ethyl acetate/90% methylene chloride to 40% ethyl acetate/60% methylene chloride) to give 239 mg (86%) of the title compound as a white solid.

Workup

  1. custompartitioned with ethyl acetate
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, 10% ethyl acetate/90% methylene chloride to 40% ethyl acetate/60% methylene chloride)

Sources & evidence

ORD record
ord-114e3a942394462e80806d7833b1dbc1
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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