Trimethylsilyldiazomethane → Methyl 6-chloro-5-nitronicotinate

HRID 1260280Notes

Reaction equation

HRID 1260280 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1>CO.C(Cl)Cl>[Cl:8][C:9]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:12]([C:13]([O:15][CH3:1])=[O:14])=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 3464596-CHLORO-5-NITRONICOTINIC ACID

Product 1

HCID 346961Methyl 6-chloro-5-nitronicotinate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(Trimethylsilyl)diazomethane (8.25 mL of a 2.00 M solution in hexanes, 16.5 mmol) was added in three portions to a stirred solution of 6-chloro-5-nitronicotinic acid (1.00 g, 4.95 mmol) in methanol (12.0 mL) and DCM (24.0 mL) at 0° C. The reaction mixture was quenched with TPA and concentrated in vacuo to afford the title compound i-2a. m/z (ES) 217 (MH)+. 1H NMR (500 MHz, CDCl3): δ 9.20 (d, 1H, J=2.1 Hz), 8.79 (d, 1H, J=2.1 Hz), 4.05 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with TPA
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1569e809016149dfb3502a727687bdc3
Source dataset
uspto-grants-2013_06
Patent number
US08470819B2

Reaction notes

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