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

HRID 1161803Notes

Reaction equation

HRID 1161803 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-fb0eacbda3ac4ab98b3c1ec2a20d7460
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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