KOTES
September 1969 were crystallized from MeOH to give a solid which was washed with Et&. Three crystallizations from Et20 gave 0.75 g of 3, mp 101-103". It was identified by spectral comparison with an authentic ample.^ Fractions 38-32 were crystallized from hIeOH to give 2 g of 1, mp 201-202". It was identical with authentic 1 previously prepared. 2-Hydroxyethyl 2,3-Bis(p-methoxyphenyl)indole-5-carboxylate (4).-.4 mixtiire of 29.1 g (0.16 mole) of p-carbethoxyphenylhydrazine3 and 41.5 g (0.16 mole) of desoxyanisoin was stirred and heated a t 160-170" (internal) for 10 min. Ethylene glycol (485 ml) was added and the mixtiire was refluxed for 22 hr. The solid obtained upon cooling and filtration was crystallized from EtOH to give 31.7 g (47%) of 4, mp 209-210", raised to 211-212" on O SH, ) X. recrystallizat'ion. Anal. ( C ? ~ H ~ B NC, 2,3-Bis(p-methoxyphenyl)indole-5-carboxylicAcid Acetone Solvate (5).--A mixture of 11 g of 4, 20 g of KOH, 80 ml of H?O, and 200 ml of EtOH was refluxed for 18 hr. The EtOH was evaporated. A solution of the residue in HZ0 was extracted with E t & and was then acidified with concentrated HC1. The solid obtained was crystallized from MezCO-H20 to give 9 g (79%) of 5 , mp 296-298' dec, raised to 297-298" by crystallization from C, N ; H : MerCO-Skellysolve B. Anal. (C23HlgN04.CBHBO) calcd, 5.84; found, 6.31. Saponification of 1 also gave 5. 5-AcetyI-2,3-bis(p-methoxypheny1)indole(6).-A mixture of 1 g of 5, 10 ml of SOclz, and 23 ml of C6H6 was refluxed for 1 hr and theii evaporated to give the acid chloride. A solut,ion of 6 ml of 3 Ji ethereal MeMgBr in 50 ml of EtzO was added to a stirred suspension of 1.80 g of CdCI, in 20 ml of Et,O. The resulting siiFpension was cooled in ice and a solution of the acid chloride i n 25 ml of Et20 was added. The mixtiire was refluxed for 4 hr, cooled in ice, treated with 50 ml of 2.5 -irHCI, and extracted with CHZCl,. The extract was washed with H,O, 1 >V NaOH, and H2O and evaporated. The resulting solid was chromatographed on Florisil using 87, ?rlenCO in Skellysolve B as the eluent. The solid fractions were crvstallixed twice from E t O h c to give 0.25 g (29%) of 6, mp 222-223'. Anal. (CP
