HCID 67271889, compound → HCID 86594753, compound

HRID 250954Notes

Reaction equation

HRID 250954 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([CH2:16][OH:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]>C(Cl)Cl.O=[Mn]=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([CH:16]=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 67271889HCID 67271889, compound

Product 1

HCID 86594753HCID 86594753, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [3-(3-nitrophenyl)-pyridin-2-yl]-methanol (69 mg, 0.30 mmol) (Agrawal, K. C. et al. J. Med. Chem. 1974, 17, 631-5) in dry CH2Cl2 (5 mL) was added activated MnO2 (90% purity, <10 micron, 251 mg, 2.89 mmol). The resulting heterogeneous mixture was stirred 2 d, at which point the black slurry was filtered through a cake of celite and washed with CH2Cl2 (3×15 mL). The combined washings were concentrated to afford 66 mg (96%) of 3-(3-nitrophenyl)-pyridine-2-carbaldehyde as a pale white solid, which was used in subsequent reactions without further purification. 1H NMR (CDCl3) δ 7.60-7.69 (m, 3H), 7.77 (dd, 1H, J=7.8, 1.5 Hz), 8.21-8.23 (m, 1H), 8.30-8.35 (m, 1H), 8.91 (dd, 1H, J=4.5, 1.5 Hz), 10.12 (s, 1H).

Workup

  1. filtrationwas filtered through a cake of celite
  2. washwashed with CH2Cl2 (3×15 mL)
  3. concentrationThe combined washings were concentrated

Sources & evidence

ORD record
ord-aa88d0a9c8184d64b65e12ffe77b4c97
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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