P-Anisidine → HCID 54889931, compound

HRID 469492Notes

Reaction equation

HRID 469492 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.O.O=[CH:11][C:12]([OH:14])=[O:13].[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>>[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH:11]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C:12]([OH:14])=[O:13])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 7732P-AnisidineHCID 581760Thiophene-3-boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 54889931HCID 54889931, compoundYield 77.4%

Conditions

Temperature
100 °C

Procedure

A mixture of thiophen-3-ylboronic acid (339 mg, 2.65 mmol), 2-oxoacetic acid hydrate (244 mg, 2.65 mmol), and 4-methoxyaniline (326 mg, 2.65 mmol) was heated under microwave irradiation at 100° C. for 1 hour. The precipitate was recovered and washed sequentially with acetonitrile, DCM and Et2O. The compound was dried under vacuum at 40° C. to obtain 2-(4-methoxyphenylamino)-2-(thiophen-3-yl)acetic acid (540 mg, 77% yield).

Workup

  1. customThe precipitate was recovered
  2. washwashed sequentially with acetonitrile, DCM and Et2O
  3. customThe compound was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-202ecd208a104a82b035afd2db57c805
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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