Methanol → Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

HRID 558208Notes

Reaction equation

HRID 558208 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([Cl:18])[C:10]=2[Cl:19])=[C:4]([Cl:20])[CH:3]=1.CO.[Si](C=[N+]=[N-])(C)(C)[CH3:24]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([O:17][CH3:24])=[O:16])=[CH:13][N:12]=[C:11]([Cl:18])[C:10]=2[Cl:19])=[C:4]([Cl:20])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 116612174-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid

Product 1

HCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinateYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid (4.3975 g, 11.2 mmol) in a mixture 70 ml MeOH and 70 ml toluene was added TMS-diazomethane (10 ml, 20 mmol, 2M/hexanes) in small portions at room temperature. At the end of the addition the suspension turned into a solution, and then a precipitate was formed again. The suspension was diluted with hexanes and filtered. And the precipitate was washed with hexanes and dried in vacuo to obtain the title compound 3.03 g (66%).

Workup

  1. additionAt the end of the addition the suspension
  2. customa precipitate was formed again
  3. filtrationfiltered
  4. washAnd the precipitate was washed with hexanes
  5. customdried in vacuo

Sources & evidence

ORD record
ord-839b90599f5a4de78ff1396b9d5b4e66
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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