HCID 22601281, compound → HCID 22601283, compound

HRID 2308287Notes

Reaction equation

HRID 2308287 reaction equation
[Cl:1][C:2]1[CH:19]=[N:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1)=[O:5]>C(Cl)Cl.CO.O=[Mn]=O>[Cl:20][C:16]1[CH:17]=[N:18][CH:19]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=1)=[O:5]

Participants

5

Reactant 1

HCID 22601281HCID 22601281, compound

Product 1

HCID 22601283HCID 22601283, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a partially dissolved solution of 3,5-dichloro-N-(4-hydroxymethyl-benzyl)-isonicotinamide (730 mg, 2.35 mmol) in CH2Cl2 (12 mL) and MeOH (1 mL) was added MnO2 (2.43 g, 23.5 mmol) and the resultant suspension was stirred at 40° C. for 16 hours. The reaction mixture was cooled to room temperature and filtered through Celite. The cake was washed with CH2Cl2/MeOH (100:3) and the filtrate was concentrated under reduced pressure to afford a crude white solid (630 mg). Purification by column chromatography on silica gel (CH2Cl2MeOH/NH4OH, 100:1:1) afforded the desired aldehyde (480 mg, 66%) as a white solid. 1H NMR (CDCl3) δ 4.78 (d, 2H, J=6.0 Hz), 6.19 (br s, 1H), 7.58 (d, 2H, J=9.0 Hz), 7.90 (d, 2H, J=9.0 Hz), 8.55 (s, 2H), 10.02 (s, 1H).

Workup

  1. filtrationfiltered through Celite
  2. washThe cake was washed with CH2Cl2/MeOH (100:3)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto afford a crude white solid (630 mg)
  5. customPurification by column chromatography on silica gel (CH2Cl2MeOH/NH4OH, 100:1:1)

Sources & evidence

ORD record
ord-7251fbab92ba44b586d3074fd7d7623b
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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