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

HRID 1766788Notes

Reaction equation

HRID 1766788 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=[C:18]([Cl:25])[C:17]=2[Cl:26])=[C:11]([Cl:27])[CH:10]=1>>[CH3:1][O:23][C:22](=[O:24])[C:21]1[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=2[Cl:27])=[C:17]([Cl:26])[C:18]([Cl:25])=[N:19][CH:20]=1

Participants

3

Reactant 2

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

Product 1

HCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

Procedure

Trimethylsilyldiazomethane (2.0 M solution in hexanes, 37 mL, 74 mmol) was added slowly to a suspension of 4-(4-bromo-2-chloro-phenylamino)-5,6-dichloro-nicotinic acid (25) (14.67 g, 37 mmol). After the addition was complete the resulting slurry was diluted with hexanes (600 mL) and the solids isolated by filtration washing with hexanes. The desired product was isolated as an off-white solid (10.06 g). The hexanes washes were concentrated and the solids passed through a plug of silica gel eluting with dichloromethane. Concentration of the product-containing fractions provided an additional 3.83 g desired product (26) for a total of 13.89 g (91%). MS (APCI+) m/z 409, 411, 413 (M+; Cl, Br pattern) detected.

Workup

  1. additionAfter the addition
  2. customthe solids isolated by filtration
  3. washwashing with hexanes

Sources & evidence

ORD record
ord-44ec15ce6c0444fa855a436838828fb6
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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