2,6-Dichlorobenzoyl chloride → HCID 57987631, compound

HRID 1869803Notes

Reaction equation

HRID 1869803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[N:10]=1.[Cl:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:28]=1[C:29](Cl)=[O:30].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[Cl:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:28]=1[C:29]([O:25][CH:20]([CH2:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH:18]=[CH:17]2)[C:21]([O:23][CH3:24])=[O:22])=[O:30]

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 57987619HCID 57987619, compound

Product 1

HCID 57987631HCID 57987631, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxypropanoate 55 (0.104 g) in pyridine (1 ml) is added 2,6-dichlorobenzoyl chloride (0.2 ml). The solution is stirred for 6 h at room temperature. A saturated solution of NaHCO3 (10 ml) is added. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with brine, dried over MgSO4 and evaporated. The residue is purified twice over silica gel using AcOEt/petroleum ether (10/90 to 20/80) as eluent.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3×10 ml)
  2. washThe organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue is purified twice over silica gel

Sources & evidence

ORD record
ord-118a77a563734e06be718a1a076cd8ed
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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