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

HRID 882779Notes

Reaction equation

HRID 882779 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 flash chromatography (gradient: 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 flash chromatography (gradient: heptane to heptane/EtOAc 7/3)

Sources & evidence

ORD record
ord-392e07fe8ef34e7d9b67a96fd6b3dd48
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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