Salicylaldehyde → HCID 136144611, compound

HRID 2227150Notes

Reaction equation

HRID 2227150 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:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH3:2].[CH:22](=O)[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25]>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:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[CH:22][C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[OH:25])[CH3:21]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 135744193HCID 135744193, compound

Product 1

HCID 136144611HCID 136144611, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a yellowish brown suspension of 0.3 g (1.06 mmol) N-Mono[4-(diethylamino)-salicylidene]-1,2-phenylenediamine from example 30 in 2 ml ethanol are added dropwise at 60° C. 129 mg (112 μl, 1.06 mmol) salicylaldehyde. The reaction slolution is stirred for 5 hours at 75° C. and after cooling to room temperature concentrated to dryness. The crude product is resolved by column chromatography (n-hexane/ethyl acetate 65:35). Yield: 139 mg (34%), colourless oil.

Workup

  1. additionare added dropwise at 60° C
  2. temperatureafter cooling to room temperature
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dc0a437255b34d1c868c7b11b19142f8
Source dataset
uspto-grants-2002_07
Patent number
US06413926B2

Reaction notes

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