2-Methoxybenzaldehyde → HCID 178489342, compound

HRID 2196567Notes

Reaction equation

HRID 2196567 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[Br:11][C:12]1[CH:18]=[C:17]([N+:19]([O-])=O)[C:15]([NH2:16])=[C:14]([CH3:22])[CH:13]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCO>[Br:11][C:12]1[CH:13]=[C:14]([CH3:22])[C:15]2[NH:16][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8][CH3:9])=[N:19][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 24489Sodium DithioniteHCID 5226794-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 178489342HCID 178489342, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

o-Anisaldehyde (0.105 ml, 0.866 mmol) and 4-bromo-2-methyl-6-nitroaniline (0.2 g, 0.866 mmol) in EtOH (3.46 ml) were treated with solid sodium dithionite (0.535 g, 2.60 mmol) and the mixture was heated to 80° C. for 16 hours following the procedure of D. Yang et. al. (Synthesis 2005, 47-56). The reaction mixture was taken to dryness and partitioned between ethyl acetate and 2N NH4OH(aq). After the usual work-up the crude material was purified by silica gel chromatography (Biotage 25S, 20% -40% ethyl acetate in hexanes) to obtained 159 (0.217 g, 0.684 mmol, 79% yield) as yellow solid. LRMS (ESI): (calc.) 316.0 and 318.0 (found) 317.1 and 319.1 (MH)+.

Workup

  1. customYang et. al. (Synthesis 2005, 47-56)
  2. custompartitioned between ethyl acetate and 2N NH4OH(aq)
  3. customAfter the usual work-up the crude material was purified by silica gel chromatography (Biotage 25S, 20% -40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-66a1cc16a5e64ccf8235055521042325
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

Loading…