Photochromic spiroindolinonaphthoxazine dye was synthesized via condensation of 1,3,3-trimethyl-2-methylene indoline with 1-nitroso-2-naphthol. Spiroindolinonaphtoxazine prepared was characterized by means of TLC, melting point measurement, UV, IR, 1H-NMR, 13C-NMR, 13C-NMR, and elemental analysis. Photophysical properties of spiroindolinonaphthoxazine were investigated using UV-visible spectrophotometer. The color-less form and the colored metastable form in ethanol solution exhibited unique characteristic bands respectively. A thermal equilibrium existed between the colorless and colored forms, and the standard enthalpy of equilibrium could be obtained from the measurement of absorbance of the colored form at different temperatures. Catalytic condensation reactions were conducted on various catalysts in order to improve the yield of spiroindolinonaphthoxazine. 5wt% Pd/C catalyst resulted in the yield about two times higher then that for nonanalytic condensation. which suggests the possibility of improvement in spiroindolinonaphthoxazine yield by the catalytic process.