Water → HCID 18999061, compound

HRID 2260798Notes

Reaction equation

HRID 2260798 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[N+:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([C:33]1[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1)[OH:32])([O-:24])=[O:23].O.C(OCC)(=O)C>CN(C)C=O>[N+:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([C:33]1[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1)=[O:32])([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 18999062HCID 18999062, compound

Product 1

HCID 18999061HCID 18999061, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridinium dichromate (18.7 g) was added to a stirred, cooled (0° C.) solution of (2-nitrophenyl)-(6-methoxypyridin-3-yl)methanol (2.0 g) in dimethylformamide (60 ml). After 2 hours at 0° C. water (100 ml) and ethyl acetate (50 ml) were added and the mixture allowed to warm to room temperature. The organic layer was separated and the aqueous extracted with ethyl acetate (3×100 ml). The combined organics were washed with water (2×100 ml) then brine (100 ml), dried (magnesium sulphate) then evaporated to dryness to give the title compound as a solid (1.90 g). mp 94°-95° C. Rf =0.35 in 33% ethyl acetate/petroleum ether (60-80) on silica plates; 1H NMR (360 MHz, CDCl3) δ 3.97 (3H, s), 6.63 (1H, d, J=9 Hz), 7.47 (1H, dd, J=1 and 8 Hz), 7.70 (1H, dd, J=8 Hz), 7.78 (1H, dd, J=8 Hz), 8.12 (1H, dd, J=3 and 9 Hz), 8.25 (1H, dd, J=1 and 8 Hz), 8.36 (1H, d, J=3 Hz); MS, m/z 258 for M+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous extracted with ethyl acetate (3×100 ml)
  3. washThe combined organics were washed with water (2×100 ml)
  4. dry with materialbrine (100 ml), dried (magnesium sulphate)
  5. customthen evaporated to dryness

Sources & evidence

ORD record
ord-410ad80e477d4a42b6fe7d1ef4e23a37
Source dataset
uspto-grants-1995_12
Patent number
US05478933

Reaction notes

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