O-Cresol → HCID 21831180, compound

HRID 1601144Notes

Reaction equation

HRID 1601144 reaction equation
Br[CH2:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.[C:12]1([CH3:19])[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>O>[CH3:19][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[O:18][CH2:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 335O-CresolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 218311782-(Bromomethyl)-3-nitropyridine

Product 1

HCID 21831180HCID 21831180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 10.4 g (48 mmol) of 2-bromomethyl-3-nitropyridine (Example 3.c), 4.8 g (44 mmol) of o-cresol, 10 g (72 mmol) of K2CO3 and 50 ml of dimethylformamide were stirred for 3 days at room temperature (approximately 25° C.). The mixture was subsequently diluted with water and extracted repeatedly using tert-butyl methyl ether. The organic phases were combined, washed and dried, and the solvent was removed under reduced pressure. The residue obtained was purified by column chromatography (cyclohexane/ethyl acetate). This gave 5 g (47%) of the title compound as a yellow oil.

Workup

  1. extractionextracted repeatedly using tert-butyl methyl ether
  2. washwashed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-8ff70a52d1bd417e9cf5a73ceb178777
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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