3-Hydroxyanthranilic Acid → Anthranilic acid, 3-hydroxy-, methyl ester

HRID 2064754Notes

Reaction equation

HRID 2064754 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.CCCCCC.[OH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]=1[NH2:24]>CO.C1(C)C=CC=CC=1>[CH3:1][O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([OH:14])[C:16]=1[NH2:24]

Participants

6

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 8058HexaneHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3-hydroxyanthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16 h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC (heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR=0.70 min; [M+H]+=168.0.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ether and EtOAc
  3. washwashed several times with water
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by CC (heptane to heptane/EtOAc 7/3)

Sources & evidence

ORD record
ord-799d51f6452840c5875e501eff442259
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

Loading…