Aniline → 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-N-phenyl-benzamide

HRID 1670076Notes

Reaction equation

HRID 1670076 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:16]=[C:17]([O:19]CC4C=CC=CC=4)[CH:18]=3)[C:13]([OH:15])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(N(CC)CC)C>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:16]=[C:17]([OH:19])[CH:18]=3)[C:13]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[O:15])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 2733179PyBroPHCID 579058343-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic Acid

Product 1

HCID 579058673-Benzo[1,3]dioxol-5-yl-5-hydroxy-N-phenyl-benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Benzo[1,3]dioxol-5-yl-5-benzyloxy-benzoic acid (500 mg), PyBroP (1.2 eq.), aniline (1.1 eq.), and triethylamine (2 eq.) were combined in dichloromethane (5 mL) and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with water. White solid which precipitated in dichloromethane layer was collected by filtration (493 mg). This material was dissolved in THF and hydrogenated over 10% Pd/C (50 mg) in Parr apparatus for 5 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to yield 362 mg of title compound (76% yield after 2 steps).

Workup

  1. washwashed with water
  2. customWhite solid which precipitated in dichloromethane layer
  3. filtrationwas collected by filtration (493 mg)
  4. dissolutionThis material was dissolved in THF
  5. waithydrogenated over 10% Pd/C (50 mg) in Parr apparatus for 5 h
  6. customThe catalyst was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. custompurified on a silica gel column

Sources & evidence

ORD record
ord-e7aea721b56a427791b3393124945344
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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