2,4-Dihydroxybenzaldehyde → HCID 136343264, compound

HRID 1582549Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[C:5]([OH:18])[C:6](=[CH:16][CH:17]=1)[CH:7]=[N:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:15].[OH:20][C:21]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:22]=1[CH:23]=O>C(O)C>[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[C:5]([OH:18])[C:6](=[CH:16][CH:17]=1)[CH:7]=[N:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]=[CH:23][C:22]1[C:21](=[CH:28][C:27]([OH:29])=[CH:26][CH:25]=1)[OH:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2.5 g (9.56 mmol) (R,R)-N-mono(4-dimethylaminosalicylidene)-1,2-cyclohexanediamine in 225 ml of ethanol is added dropwise at room temperature over the course of 45 minutes a solution of 1.321 g (9.56 mmol) 2,4-dihydroxybenzaldehyde in 225 ml ethanol. The reaction solution is heated at 60° C. for 4 h. After cooling to room temperature the resultant reddish brown solution is concentrated to dryness. The crude product (ca. 5 g) is resolved by column chromatography (ethyl acetate/methanol 9:1). Yield: 1,09 g (300%), yellowish orange solid.

Workup

temperatureAfter cooling to room temperature the resultant
concentrationis concentrated to dryness

Sources & evidence

ORD record: ord-5049e970dbea4f218476c7ef911ed209
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737391B2

Reaction notes

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