Triethylamine → 3-Phenoxy-N-quinolin-6-yl-benzamide

HRID 2080268Notes

Reaction equation

HRID 2080268 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[O:12]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[O:12]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)=[O:23])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113736-AminoquinolineHCID 195393-Phenoxybenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 588753273-Phenoxy-N-quinolin-6-yl-benzamideYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-aminoquinoline (250 mg, 1.04 mmol) in N,N-dimethylformamide (15 mL) were added 3-phenoxybenzoic acid (371 mg, 1.73 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (722 mg, 1.90 mmol) and triethylamine (603 μl, 4.33 mmol), and the solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate, the organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), and the title compound (328 mg, 0.964 mmol, 93%) was obtained.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-63711274aac54efbb2096ce7389fc771
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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