Methyl4,6-dichloronicotinate → Methyl 4-(1H-1,2,3-benzotriazol-1-yl)-6-chloronicotinate

HRID 1896515Notes

Reaction equation

HRID 1896515 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=[C:13]([Cl:21])[CH:12]=1>CCOC(C)=O>[N:1]1([C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=[C:13]([Cl:21])[CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 2764083Methyl4,6-dichloronicotinateHCID 178418385HCID 178418385, compound

Product 1

HCID 59198426Methyl 4-(1H-1,2,3-benzotriazol-1-yl)-6-chloronicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A 1:1 mixture of benzotriazole and methyl 4,6-dichloronicotinate was heated neat in a preheated oil bath at 150° C. for a period of 10-15 min. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed successively with saturated NaHCO3 and brine. The organic phase was separated, dried over MgSO4 and filtered. After evaporation of the organic solvent, the isomers in the residue were purified and separated by flash chromatography (10-70% EtOAc in hexanes) to provide the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed successively with saturated NaHCO3 and brine
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customAfter evaporation of the organic solvent
  7. customthe isomers in the residue were purified
  8. customseparated by flash chromatography (10-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-78c48cddfff94a6aabd44364667ec744
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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