Aniline → HCID 58557005, compound

HRID 469445Notes

Reaction equation

HRID 469445 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.O.O=[CH:21][C:22]([OH:24])=[O:23]>C(#N)C>[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13]([CH:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:22]([OH:24])=[O:23])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58557005HCID 58557005, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of aniline (0.30 ml, 3.27 mmol), 6-methoxypyridin-3-ylboronic acid (500 mg, 3.27 mmol) and 2-oxoacetic acid hydrate (301 mg, 3.27 mmol) in acetonitrile (20 ml) was heated under microwave irradiation at 100° C. for 1 hour. The reaction mixture was evaporated to dryness, and the crude product was triturated with acetonitrile. The solid was collected by suction filtration to get 2-(6-methoxypyridin-3-yl)-2-(phenylamino)acetic acid (202 mg, 23% yield).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product was triturated with acetonitrile
  3. filtrationThe solid was collected by suction filtration

Sources & evidence

ORD record
ord-679a5018a0394ba88b06c3cff4c8b83c
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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