Trimethylsilyldiazomethane → methyl 2-amino-4-chloro-5-methoxybenzoate

HRID 482013Notes

Reaction equation

HRID 482013 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][Si](C=[N+]=[N-])(C)C>CO>[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 190649652-AMino-4-chloro-5-Methoxy-benzoic acid

Product 1

HCID 19064933methyl 2-amino-4-chloro-5-methoxybenzoateYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-4chloro-5-methoxybenzoic acid (3.0 g, 15.0 mmol; prepared according to the procedure of Denny, et al., J. Med. Chem. 34:217-222 (1991)) in 70 ml MeOH was treated with excess trimethylsilyl diazomethane. The solution was concentrated and the residue flash chromatographed on silica (9:1 hexane/EtOAc to give the title compound (46%): mp 63°-64° C.; 1H NMR (300 MHz, CDCl3) δ 6 3.83 (s, 3H), 3.90 (s, 3H), 5.48 (bs, 2H), 6.75 (s, 1H), 7.39 (s, 1H); MS (DCI/NH3) m/z 216 (M+H)+.

Workup

  1. customprepared
  2. concentrationThe solution was concentrated
  3. customthe residue flash chromatographed on silica (9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-2051251030fc40e2983054b5acb85699
Source dataset
uspto-grants-1998_08
Patent number
US05792767

Reaction notes

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