2,6-Dichlorobenzaldehyde → HCID 86602771, compound

HRID 1180798Notes

Reaction equation

HRID 1180798 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:29]=1[CH:30]=O.[OH-].[Na+]>CO>[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:29]=1[CH:30]=[CH:2][C:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 58980322HCID 58980322, compound

Product 1

HCID 86602771HCID 86602771, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution at room temperature of III (150 mg, 0.42 mmol), 2,6-dichlorobenzaldehyde (148 mg, 0.85 mmol) or aldehyde (1.5–2.0 equiv.) in MeOH (10 ml) was added a solution of NaOH (1.7 ml, 1N in H2O). A pale yellow precipitate appeared. After 3 days, the reaction mixture was filtered off, rinsed with H2O. The solid residue was then dissolved in AcOEt, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was finally purified by flash chromatography on silica gel (AcOEt/hexane:20/80→40/60) to afford the title compound IVc (185 mg, 0.36 mmol, 85% yield) as a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.48 (bs, 1H), 8.11 (s, 4H), 7.96 (d, J=17.1 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H), 7.68 (d, J=16.3 Hz, 1H), 7.42 (d, J=7.9 Hz, 2H), 7.35–7.15 (m, 4H), 6.68 (s, 1H), 1.54 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered off
  2. washrinsed with H2O
  3. dissolutionThe solid residue was then dissolved in AcOEt
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was finally purified by flash chromatography on silica gel (AcOEt/hexane:20/80→40/60)

Sources & evidence

ORD record
ord-99142e092dec4bc89dd5e7104ed8d083
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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