2-Methoxybenzaldehyde → HCID 59843298, compound

HRID 2196569Notes

Reaction equation

HRID 2196569 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[N+:11]([C:14]1[C:15]([NH2:21])=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]>C(O)C>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]1[NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([N+:11]([O-:13])=[O:12])[C:15]=2[N:21]=1

Participants

4

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 59843298HCID 59843298, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of o-anisaldehyde (0.789 ml, 6.53 mmol) and 3-nitro-o-phenylenediamine (1 g, 6.53 mmol) in ethanol (30 ml) was heated to 90° C. for 20 hours in a sealed tube. The red reaction mixture was taken to dryness and purified by silica gel chromatography (Biotage 40M, 75% DCM in hexanes to 100% DCM) to give 163 (0.62 g, 2.303 mmol, 35.3% yield) as yellow solid. LRMS (ESI): (calc.) 269.3 (found) 270.1 (MH)+.

Workup

  1. customThe red reaction mixture
  2. custompurified by silica gel chromatography (Biotage 40M, 75% DCM in hexanes to 100% DCM)

Sources & evidence

ORD record
ord-1500901179b946a390bee9033ecdc478
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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