Sodium Hydroxide → Amino-naphthalen-2-yl-acetic acid
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[NH:15]C(=O)N[C:12]1=[O:17].[OH-:18].[Na+]>>[NH2:15][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([OH:17])=[O:18]Participants
3
Procedure
A solution of 5-(2-naphthyl) hydantoin (10g., 44.5 mmole) in 10% sodium hydroxide solution (50 ml.) was heated under reflux for 18 hours. The solution was cooled, filtered, diluted and treated with concentrated hydrochloric acid to bring the pH to 5.0. The resulting solid was filtered off washed with water and added to 5N-hydrochloric acid (2 L). Insoluble material was filtered off and the filtrate was taken to pH 5.0 with 40% sodium hydroxide solution. On standing, the amino-acid crystallised out as platelets (3.92 g.) m.p. 238°-240°, λλmax. (pH 6.0 phosphate) 225 ε 51,700), 276 (ε 3,520), 268 nm. (ε 3,420).
Workup
- temperatureunder reflux for 18 hours
- temperatureThe solution was cooled
- filtrationfiltered