TABLE I 3-R-2-( 2-~APHTHYL)CIXCHONIXICACIDS 7
R
Q
Alp, OC dec
Yield, Yc
Neut equiv
-
Calcd--C, Yc
n, R
I1 245-247" 96 CHa 289-290b 90 CZHj 310-3 11" 62 48 34 1 SO. 99 262-263 5.B2 n-CaH7 51 356 81.0Y 261-262 5.95 n-CaHQ 33 355 81.09 289-290 5.95 i-C4Hs 56 369 81.27 6.23 273-274 n-CiH,, 46 384 81.44 6.57 n-CsH13 2 55-2 8 7 56 398 81.59 6.85 n-C7Hlj 180-191 81.83 201-202 28 426 7.34 n-CsH19 16 454 82.08 7.77 183-184 n-CllH23 P. K. Bose and N. C. Guga [J.Indian Chenc. SOC.,13, 700 (1936)l reported mp 248'.
General Procedure for Synthesis of 3-Substituted 2-(2-Naphthy1)quinoline Picrates.-Approximately 1.O g of a cinchoninic acid was intimately mixed with 0.3 g of copper powder9 and heated on a sand bath at 1 mm pressure. In most cases, it was necessary for the bath temperature to be 270-300". Picrate derivatives were obtained by the action of a saturated ethanolic solution of picric acid with each quinoline distillate. Results are shown in Table 11.
336 so. 88 353 81.08 365 81.28 367 S I . 04 381 81.37 39 1 81.55 422 81.76 454 81,86 Lit.7bmp 285-286". Lit.7bmp
latter was also obtained from the corresponding i.othioiuoniiim chloride (11) which was synthesized by treatment of I with thiourea. 2-Amino-4-n-butylami110-5-(p-chloropheiiylazo)-6-p~-rimidinol ( I X ) was synthesized from 2-amino-4-n-butylamino6-pyrimidino14(VIII)and p-chlorophenyldiazonium chloride. SCHEME I 6-C1
TABLE I1 3-R-2-(2-"aPHTHYL)QUINOLlNE
R
H n-CaH7 n-CdH9 i-C4H5 n-CiH11 n-C6& n-C~Hls n-CsHls n-CllH23
blp,
=c
161-162 195-196 203-204 dec 197-198 190-191 172-173 7 53-154 127-128 107-108
5.24 598 5.84 6.23 6.47 6.93 7.37 7.79 314-315".
"
