4-Formylbenzoic acid → HCID 22478646, compound

HRID 736507Notes

Reaction equation

HRID 736507 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1.[CH:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=O.[Sn](CCCC)(CCCC)(Cl)Cl.C1([SiH3])C=CC=CC=1>COCCOC>[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 120884-Formylbenzoic acidHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 22478631HCID 22478631, compound

Product 1

HCID 22478646HCID 22478646, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of aniline 456b (509 mg; 2.8 mmol); 4-formylbenzoic acid (426 mg; 2.8 mmol) and Bu2SnCl2 (198 mg; 0.65 mmol; 23% mol) in DME (14 mL) was stirred at room temperature for 3 min and treated with neat PhSiH3 (0.6 mL; 4.7 mmol; 1.7 mmol) and allowed to react for 18 h. After quenching the excess of silane with MeOH, the mixture was concentrated and purified by chromatographic column on silica gel (elution 5% MeOH in DCM) to give 729 mg (2.54 mmol; 91% yield) of acid 456c.

Workup

  1. customto react for 18 h
  2. customAfter quenching the excess of silane with MeOH
  3. concentrationthe mixture was concentrated
  4. custompurified by chromatographic column on silica gel (elution 5% MeOH in DCM)

Sources & evidence

ORD record
ord-2c9ec1993ffd4c8789fb506e97d19152
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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