Sulfuric acid magnesium salt (1:1) → methyl 4-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-2-hydroxybenzoate

HRID 1392278Notes

Reaction equation

HRID 1392278 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][NH2:15])=[CH:6][C:5]=1[OH:16].[CH2:18]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[CH:34]=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:34]/[C:26]2[N:25]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:33]3[C:28]([CH:27]=2)=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:6][C:5]=1[OH:16]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 129167171-benzyl-1H-indole-2-carbaldehydeHCID 691961504-(3-Aminooxy-propoxy)-2-hydroxy-benzoic acid methyl ester

Product 1

HCID 87729992methyl 4-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-2-hydroxybenzoateYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-aminooxy-propoxy)-2-hydroxy-benzoic acid methyl ester (0.17 g, 0.69 mmol) and 1-benzyl-1H-indole-2-carbaldehyde (0.16 g, 0.69 mmol) in methylene chloride (10 mL) was added anhydrous magnesium sulfate (0.04 g). The mixture was allowed to stir at ambient temperature overnight, then heated to reflux for 1 hour and allowed to cool back to ambient temperature. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give 4-[3-({[(1E)-(1-benzyl-1H-indol-2-yl)methylidene]amino}oxy)propoxy]-2-hydroxybenzoic acid methyl ester (0.11 g, 36%) as a white solid. 1H NMR (400 MHz, CDCl3); δ 10.94 (s, 1H), 8.16 (s, 1H), 7.70 (d, 1H), 7.63 (d, 1H), 7.28-7.17 (m, 5H), 7.11 (t, 1H), 7.00 (d, 2H), 6.78 (s, 1H), 6.41 (s, 1H), 6.39 (d, 1H), 5.72 (s, 2H), 4.21 (t, 2H), 3.98 (t, 2H), 3.89 (s, 3H), 2.03 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureto cool back to ambient temperature
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-296ab8fc83b140629fe490ea2b372367
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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