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4-Aminobenzonitrile → HCID 59517247, compound

HRID 2079096
Notes
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Reaction equation

HRID 2079096 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][C:12]=1[CH:13]=O.C[Si]([C:27]#[N:28])(C)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>ClCCl.O.C(OCC)(=O)C>[C:27]([CH:13]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:12]1[CH:15]=[C:16]([O:21][CH3:22])[CH:17]=[C:18]([O:19][CH3:20])[C:11]=1[F:10])#[N:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 133964-AminobenzonitrileHCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 13861691HCID 13861691, compound

Product 1

HCID 59517247HCID 59517247, compound

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

After adding 1.23 g of 4-aminobenzonitrile [CAS No. 873-74-5], 1.92 g of 2-fluoro-3,5-dimethoxybenzaldehyde [CAS No. 113984-71-7], 1.0 g of MS3A and 2.77 ml of trimethylsilyl cyanide to a solution of 0.645 g of Yb(OTf)3 in 20 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 20 hours. After then adding 500 ml of ethyl acetate and 300 ml of water to the reaction mixture, it was filtered through celite and the celite was washed with 500 ml of ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (2.59 g) as a white solid.

Workup

  1. filtrationwas filtered through celite
  2. washthe celite was washed with 500 ml of ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-2e54b9bab9af4927b696c3726c165e2d
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928228B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes