ChemicalBook CAS DataBase List AMINO(3-BROMOPHENYL)ACETIC ACID

AMINO(3-BROMOPHENYL)ACETIC ACID synthesis

3synthesis methods

Product Name:AMINO(3-BROMOPHENYL)ACETIC ACID
CAS Number:150174-93-9
Molecular formula:C8H8BrNO2
Molecular Weight:230.06

79422-72-3 Synthesis

5-(3-bromophenyl)imidazolidine-2,4-dione

79422-72-3
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150174-93-9
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Yield:-

Reaction Conditions:

Stage #1: 5-(3-Bromphenyl)hydantoinwith sodium hydroxide;water at 20; for 240 h;Heating / reflux;
Stage #2: with acetic acid in water; pH=7;

Steps:

19

A stirred mixture of 5-(3-bromophenyl)-2,4-imidazolidinedione (prepared using a similar method to that disclosed in Pharmazie 1981 , 36, 467) (7.8g, 30.6mmol) and sodium hydroxide (1Og, 250mmol) in water (100ml) was heated under reflux for 4 days, then allowed to cool to room temperature and stand for 6 days. The stirred reaction mixture was then treated with acetic acid to pH 7 and the resulting precipitate filtered off, washed with water and dried under vacuum to leave a white solid. This material was suspended in water (200ml), adjusted to pH 2 by addition of cone HCI acid and then stirred vigorously for 2 hours. The remaining solid was filtered off and the filtrate adjusted to pH 7 by addition of cone. NaOH solution producing a precipitate. This mixture was cooled to 7⁰C by standing in a fridge for 2 hours, then the solid was filtered off, washed with water and dried under vacuum at 5O⁰C to afford the title compound as a white solid (5.7Og). 1H NMR (D₆-DMSO) δ: 4.25 (1 H, s), 7.30 (1 H, m), 7.40 (1 H, d), 7.50 (1 H, d), 7.63 (1 H, s). OH and NH₂ signals obscured by broad peaks at 3.34 and 8.05.

References:

WO2009/34061,2009,A1 Location in patent:Page/Page column 44-45

773837-37-9 Synthesis