3-Bromobenzoic acid → 3-((3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)hydroxymethyl)benzoic acid

HRID 326899

Reaction equation

HRID 326899 reaction equation
[Li][Li].Br[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH:24]=[CH:25][C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[CH:29]=[O:30])=[N:21]2)=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH:24]=[CH:25][C:26]3[CH:27]=[C:28]([CH:29]([OH:30])[C:4]4[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=4)[C:7]([OH:9])=[O:8])[CH:31]=[CH:32][CH:33]=3)=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 114563-Bromobenzoic acidHCID 139759Lithium, mol. (Li2)HCID 533948533-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde

Product 1

HCID 541291983-((3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)hydroxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To the dilithium salt (5.92 mmol) obtained from 3-bromobenzoic acid (W. E. Parham and Y. A. Sayed, J. Org. Chem., 39, 2051 (1974)), a solution of 3-(2-(7-chloro-2-quinolinyl)ethenyl)benzaldehyde (1.503 g, 5.12 mmol) (U.S. Pat. No. 4,851,409, Jul. 25, 1989, Example 24, Step 1) in THF (25 mL) was added dropwise at -78° C. The mixture was stirred for 2 h at -78° C. and was quenched with 25% aqueous NH4OAc. The mixture was acidified to pH 5 with AcOH and extracted with EtOAc. The organic fractions were dried over Na2SO4 and evaporated. Flash chromatography of the residue on silica using EtOAc:toluene:AcOH 30:70:1 yielded the title compound.

Workup

  1. customwas quenched with 25% aqueous NH4OAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic fractions were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-23cdb75967a74c6db07501946e8f41b2
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Linked notes

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