4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46841007, compound

HRID 1846303Notes

Reaction equation

HRID 1846303 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)=[O:5].[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=1[CH3:33]>C(O)C.[Cu](Cl)Cl>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:17][CH:16]=[C:15]([O:18][CH3:19])[CH:14]=3)[N:1]=[C:28]2[C:27]2[CH:30]=[C:31]([CH3:32])[C:24]([O:23][CH2:22][CH2:21][OH:20])=[C:25]([CH3:33])[CH:26]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehydeHCID 54877884HCID 54877884, compound

Product 1

HCID 46841007HCID 46841007, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-bromo-phenyl)-5-methoxy-benzamide (0.240 g, 0.740 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.145 g, 0.740 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.298 g, 2.22 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with ethyl acetate (100 mL) and water (100 mL). After separation the organic phase was further backwashed with water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated. The crude was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give the title compound as white solid. Yield: 120 mg (33%). MP 160-162° C. 1H-NMR (400 Hz, CDCl3): δ 7.74 (d, 1H), 7.69 (s, 1H), 7.46 (d, 2H), 7.40 (m, 1H), 7.03 (d, 2H), 6.96 (s, 2H), 3.94 (s, 3H), 3.91 (m, 2H), 3.82 (t, 2H), 2.17 (s, 6H), 2.05 (t, 1H). MS (ES+) m/z: 497.41 (M+1).

Workup

  1. temperatureat reflux for 4 hours under nitrogen
  2. customThe solvent was removed
  3. additionthe residue was diluted with ethyl acetate (100 mL) and water (100 mL)
  4. customAfter separation the organic phase
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-435287e521fb461ebe3711b240285e4e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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