Methyl Anthranilate → HCID 58557011, compound

HRID 469511Notes

Reaction equation

HRID 469511 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].O.O=[CH:25][C:26]([OH:28])=[O:27]>C(#N)C>[CH3:18][O:17][C:15]([C:14]1[CH:19]=[CH:20][CH:21]=[CH:22][C:13]=1[NH:12][CH:25]([C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:26]([OH:28])=[O:27])=[O:16]

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58557011HCID 58557011, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxypyridin-3-ylboronic acid (200 mg, 1.31 mmol), methyl 2-aminobenzoate (170 μl, 1.31 mmol), and 2-oxoacetic acid hydrate (120 mg, 1.31 mmol) in acetonitrile (20 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified by flash-chromatography (DCM/MeOH=9/1) to obtain 2-(2-(methoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (118 mg, 28.5% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by flash-chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-e9609f57010e4b42b7244ee374d31a82
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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