Methyl 4-Formylbenzoate → HCID 4915285, compound

HRID 579458Notes

Reaction equation

HRID 579458 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.S(=O)(O)[O-].[Na+]>CO>[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:10][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=3[N:9]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 1534044-Methoxy-o-phenylenediamineHCID 23665763Sodium Bisulfite

Product 1

HCID 4915285HCID 4915285, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Methoxybenzene-1,2-diamine (1.96 g, 14.2 mmol), 4-formylbenzoic acid methyl ester (2.33 g, 14.2 mmol) and sodium bisulphite (1.55 g, 14.9 mmol) were refluxed in methanol (50 mL) for 3 h, then evaporated to dryness. The solid residue was partitioned between dichloromethane and water. The organic layer was dried, evaporated and purified by column chromatography, eluting with. The title compound (2.65 g, 9.40 mmol, 66%) was obtained as a dark solid.

Workup

  1. customevaporated to dryness
  2. customThe solid residue was partitioned between dichloromethane and water
  3. customThe organic layer was dried
  4. customevaporated
  5. custompurified by column chromatography
  6. washeluting with

Sources & evidence

ORD record
ord-b79c06edb0824200be7563693d7f2b00
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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