Sodium Hydroxide → HCID 19004423, compound

Reaction equation

C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH:12]=[O:13])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[O:16][CH2:15][CH2:14][N:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:10][CH:9]=1)[CH:12]=[O:13]

Participants

Procedure

A solution of 4-[N-[2-(2-naphthalenyloxy)ethyl]formamido]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in hot methanol (5 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (3.0 mL) and the mixture was concentrated to remove the organic solvents. The residue, in water, was treated with 2N hydrochloric acid and the mixture was chilled, filtered, and washed with water. The solids were dissolved in a mixture of tetrahydrofuran and dichloromethane, dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane provided 0.4 g of purified 4-[N-[2-(2-naphthalenyloxy)ethyl]formamido]-alpha-oxobenzeneacetic acid as a yellow solid, mp 172° C. with decomposition.