Hydrochloric Acid → 5-Nitro-2-(pyridin-2-ylmethoxy)benzaldehyde

HRID 550418Notes

Reaction equation

HRID 550418 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Cl.Cl>CN(C=O)C.C(Cl)Cl>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)=[C:3]([CH:6]=1)[CH:4]=[O:5])([O-:12])=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 668085-Nitrosalicylaldehyde

Product 1

HCID 167691365-Nitro-2-(pyridin-2-ylmethoxy)benzaldehydeYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-hydroxy-5-nitrobenzaldehyde (5.0 g, 29.9 mmol), potassium carbonate (4.12 g, 29.9 mmol) and caesium carbonate (9.74 g, 29.9 mmol) were mixed in DMF (30 ml). Picolyl chloride.HCl (5.39 g, 32.9 mmol) was added and the mixture then heated at 100° C. for 5 hours. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, dried and evaporated. Trituration of the residue in ether provided 5-nitro-2-(pyridin-2-ylmethoxy)benzaldehyde as a tan solid (4.87 g, 63%); NMR Spectrum: 5.54 (s, 2H), 7.40 (dd, 1H), 7.56 (d, 1H), 7.69 (d, 1H), 7.89 (t, 1H), 8.47-8.51 (m, 2H), 8.60 (d, 1H), 10.44 (s, 1H); Mass Spectrum: 259 (MH+).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-a455b8d6ed4c4d0197edb656439fc91a
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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