4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46841008, compound

HRID 1846306Notes

Reaction equation

HRID 1846306 reaction equation
[NH2:1][C:2]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[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](=[C:17]([O:18][CH3:19])[CH:16]=[CH:15][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 59020725HCID 59020725, compound

Product 1

HCID 46841008HCID 46841008, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-bromo-phenyl)-3-methoxy-benzamide (0.600 g, 1.86 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.360 g, 1.86 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.750 g, 5.58 mmol). The reaction mixture was stirred at reflux for 16 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), then brine (100 mL), dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1) to give the title compound as a white solid. Yield: 250 mg (27%). MP 100-102° C. 1H-NMR (400 Hz, CDCl3): δ 7.90 (d, 1H), 7.47 (m, 3H), 7.25 (m, 1H), 7.03 (d, 2H), 7.00 (s, 2H), 4.02 (s, 3H), 3.91 (m, 2H), 3.80 (t, 2H), 2.15 (s, 6H), 2.06 (t, 1H). MS (ES+) m/z: 497.41 (M+1).

Workup

  1. temperatureat reflux for 16 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
  5. dry with materialbrine (100 mL), dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (SiO2, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0399d3679cfb4c37897db036dffd3c6e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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