1,4-Dioxane → 5-Nitropyridine-2-carbaldehyde

HRID 1198727Notes

Reaction equation

HRID 1198727 reaction equation
C[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[O:11]1CCOC[CH2:12]1>CCOC(C)=O>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([CH:12]=[O:11])=[N:3][CH:2]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 3293602-Methyl-3-nitropyridine

Product 1

HCID 151455015-Nitropyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Nitropyridine-2-carboxaldehyde was prepared from the nitro derivative, 2-methyl-3-nitropyridine, by the procedure employed for the synthesis of Example I, except that anhydrous dioxane was used as the solvent and the reaction time was 4 h. Yield: 2.0 g (42%); mp 66°-67° C. (lit. 66.5°-67.5° C.); TLC, Rf 0.85 (EtOAc); 1H NMR (90 MHz, CDCl3) δ 8.0 (d, 1H, 3-H, J3,4 =4.5 HZ), 8.30 (d, 1H, 4-H, J3,4 =4.5 Hz), 9.25 (s, 1H, 6-H), 10.45 (s, 1H, 2-CHO).

Workup

  1. custommp 66°-67° C. (lit. 66.5°-67.5° C.)

Sources & evidence

ORD record
ord-a22fdfd76c9e4974b30ed9ddfb75383e
Source dataset
uspto-grants-1994_01
Patent number
US05281715

Reaction notes

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