2-Hydroxy-4-Methoxybenzaldehyde → HCID 136388372, compound

HRID 2227148Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 2.5 g (8.64 mmol) of (R,R)-N-mono[4-(diethylamino)salicylidene]-1,2-cyclohexanediamine in 200 ml of ethanol is added dropwise over the course of 45 minutes at room temperature a solution of 1.3 g (8.64 mmol) of 4-methoxysalicylaldehyde in 200 ml of ethanol. The reaction solution is heated at 60° C. for 4 h. After the reaction solution has been cooled to room temperature it is concentrated to dryness. The crude product obtained is purified by column chromatography (ethyl acetate/methanol 9:1). Yield: 500 mg (14%), reddish orange oil, which slowly crystallizes.

Workup

temperatureAfter the reaction solution has been cooled to room temperature it
concentrationis concentrated to dryness

Sources & evidence

ORD record: ord-a498fe644d474c9abc28dfb03760d9c4
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413926B2

Reaction notes

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