O-Phenylenediamine → HCID 135744193, compound

HRID 2227149Notes

Reaction equation

HRID 2227149 reaction equation
[CH2:1]([N:3]([C:6]1[CH:7]=[C:8]([OH:14])[C:9](=[CH:12][CH:13]=1)[CH:10]=O)[CH2:4][CH3:5])[CH3:2].[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]>C(O)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:6]1[CH:7]=[C:8]([OH:14])[C:9](=[CH:12][CH:13]=1)[CH:10]=[N:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH2:22])[CH3:2]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 135744193HCID 135744193, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.479 g (17.64 mmol) 4-(N,N-Diethylamino)-salicylaldehyde are added at 5° C. in portions to a solution of 1.927 g (17.64 mmol) 1,2-phenylenediamine in 18 ml ethanol, the temperature being kept below 10° C. The resultant dark red suspension is stirred for 8 hours at room temperature and concentrated to dryness in vacuo. The crude product (6.34 g) is resolved by column chromatography (n-hexane/ethyl acetate 65:35). Yield: 1.27 g (26%), golden yellow crystalls.

Workup

  1. custombeing kept below 10° C
  2. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-324d85799535445a8b1c52a00d9377b5
Source dataset
uspto-grants-2002_07
Patent number
US06413926B2

Reaction notes

Loading…