Benzene → Methyl 2-amino-6-chlorobenzoate

HRID 2117272Notes

Reaction equation

HRID 2117272 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:10]=1[C:11]([OH:13])=[O:12].C1C=CC=CC=1>CO>[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:10]=1[C:11]([O:13][CH3:1])=[O:12]

Participants

5

Reactant 3

HCID 241BenzeneHCID 750712-Amino-6-chlorobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 592849Methyl 2-amino-6-chlorobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To prepare this compound, trimethylsilyldiazomethane (2 M in hexanes, 1.5 equiv) was added to a solution of the 2-amino-6-chlorobenzoic acid (1 equiv) in 2:1 benzene:methanol (0.2-0.3 M) at room temperature. After 1 hour, the solvent was removed under reduced pressure to afford methyl 2-amino-6-chlorobenzoate in 96% yield. That product was used without further purification or was purified by flash chromatography (7:3 hexanes:ethyl acetate) in 91% yield.

Workup

  1. customat room temperature
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-187d3b9512b04db2bddd30c568e2f736
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Reaction notes

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