Trimethylsilyldiazomethane → Methyl 3-amino-4-nitrobenzoate

HRID 272705Notes

Reaction equation

HRID 272705 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]([OH:14])=[O:13]>C(Cl)Cl.CO>[NH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]([O:14][CH3:1])=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2280713-amino-4-nitrobenzoic acid

Product 1

HCID 15892778Methyl 3-amino-4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(Trimethylsilyl)diazomethane (6 mL, 2M solution in hexanes) was added to a solution of 3-amino-4-nitro-benzoic acid in CH2Cl2 (25 mL) and methanol (25 mL). Stirred at room temperature until bubbling ceased. Concentrated under vacuum to provide 1.2 g of desired product. MS (DCI) m/e 197 (M+H)+.

Workup

  1. customuntil bubbling
  2. concentrationConcentrated under vacuum

Sources & evidence

ORD record
ord-44901b9acb914f8994b575117f99a85a
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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