Trimethylsilyldiazomethane → 6-Fluoro-3-nitro-2-phenylaminobenzoic acid methyl ester

HRID 242976Notes

Reaction equation

HRID 242976 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[F:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]([N+:25]([O-:27])=[O:26])=[CH:11][CH:10]=1>CO.C(Cl)Cl>[CH3:1][O:16][C:15](=[O:17])[C:14]1[C:9]([F:8])=[CH:10][CH:11]=[C:12]([N+:25]([O-:27])=[O:26])[C:13]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 681578336-Fluoro-3-nitro-2-phenylaminobenzoic acid

Product 1

HCID 681578036-Fluoro-3-nitro-2-phenylaminobenzoic acid methyl esterYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyldiazomethane (2M in hexane, 7.24 mL, 14.5 mmol) was added dropwise to a solution of 6-fluoro-3-nitro-2-phenylaminobenzoic acid (2.0 g, 7.24 mmol) in MeOH (5 mL) and DCM (40 mL) at RT. The solution was stirred at RT for 45 min then the volatiles were removed under reduced pressure to afford the title compound (2.1 g, quantitative). 1H NMR (CDCl3, 400 MHz): δ 9.67 (1H, br s), 8.32 (1H, dd, J=9.47, 5.75 Hz), 7.36-7.30 (2H, m), 7.23-7.07 (3H, m), 6.64 (1H, dd, J=9.47, 8.33 Hz), 3.27 (3H, s)

Workup

  1. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-a40650d2cb0546b4a32535de50673e47
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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