3-Chlorobenzaldehyde → HCID 69197213, compound

HRID 2116513Notes

Reaction equation

HRID 2116513 reaction equation
C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13](I)=[CH:12]2.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23]>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]([C:13]2[CH:14]=[N:15][C:16]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:6])[OH:23])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 534386358-Chloro-3-iodoquinolineHCID 178418918HCID 178418918, compound

Product 1

HCID 69197213HCID 69197213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

iso-Propyl magnesium chloride (2M solution in tetrahydrofuran)(3.76 ml, 7.5 mmol) was added dropwise over 0.25 h to a stirred solution of 8-chloro-3-iodoquinoline (D1)(2.0 g, 6.9 mmol) in tetrahydrofuran (16 ml) at −40° C. under argon. After stirring the solution at this temperature for 0.5 h, 3-chlorobenzaldehyde (0.77 ml, 6.8 mmol) was added dropwise over 10 mins. The solution was allowed to warm to ambient temperature over 1 h and then quenched by the addition of a saturated solution of sodium chloride (100 ml). The mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (D2) as a crude solid (1.84 g, 6.0 mmol, 88%) which was used directly in the next stage (see D3).

Workup

  1. customquenched by the addition of a saturated solution of sodium chloride (100 ml)
  2. extractionThe mixture was extracted with ethyl acetate (2×100 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03bd230e70e74aafa0fd095f11d4ba76
Source dataset
uspto-grants-2008_10
Patent number
US07439243B2

Reaction notes

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