Sodium Hydroxide → HCID 23669969, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[OH-].[Na+:15]>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O-:13])=[O:12].[Na+:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2-nitrophenyl)acetic acid (18.1 g) in normal sodium hydroxide solution (120 cc) is hydrogenated in an autoclave under a pressure of 5 bar for 2.5 hours at 20° C. in the presence of 3% palladium-on-carbon black (1.5 g). The solution of sodium (2-aminophenyl)acetate thus obtained is cooled to +5° C. and then treated with a solution of di-tert-butyl dicarbonate (26.16 g) in tetrahydrofuran (100 cc) and then with normal sodium hydroxide solution (80 cc). The reaction mixture is stirred at 20° C. for 80 hours, partially concentrated under reduced pressure (2.7 kPa), diluted with water (200 cc) and washed with ethyl ether (3×200 cc). The aqueous phase is acidified to pH 3 by addition of 4N hydrochloric acid and extracted with ethyl acetate (2×200 cc). The combined organic phases are washed with water (2×150 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). (2-tert-Butoxycarbonylaminophenyl)acetic acid (25 g) is obtained in the form of a cream-white solid.
Sources & evidence
- ORD record
- ord-d48933faaff34b739f176d795a371b2e
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05102667
Reaction notes
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