2,4-Dihydroxybenzaldehyde → HCID 136343263, compound

HRID 2227147Notes

Reaction equation

HRID 2227147 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].[OH:22][C:23]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:24]=1[CH:25]=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:25][C:24]1[C:23](=[CH:30][C:29]([OH:31])=[CH:28][CH:27]=1)[OH:22])[CH3:21]

Participants

4

Reactant 2

HCID 72132,4-DihydroxybenzaldehydeHCID 135581365HCID 135581365, compound

Product 1

HCID 136343263HCID 136343263, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 at room temperature over the course of 45 minutes a solution of 1.19 g (8.64 mmol) of 2,4-dihydroxybenzaldehyde. The suspension is heated at 60° C. for 4 h. After cooling to room temperature the resultant brownish orange solution is concentrated to dryness. The crude product (3.5 g) is resolved by column chromatography (ethyl acetate/methanol 9:1). Yield: 570 mg (16%), yellowish orange solid.

Workup

  1. temperatureAfter cooling to room temperature the resultant brownish orange solution
  2. concentrationis concentrated to dryness

Sources & evidence

ORD record
ord-ff0902ba1c584dd5afa619b784c5fd99
Source dataset
uspto-grants-2002_07
Patent number
US06413926B2

Reaction notes

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