Reference

Dichroic azo dyes

Dichroic azo dyes. Hallas, Geoffrey; Jones, Francis (Rank Organisation Ltd., Engl.). Ger. Offen. DE 2640624 17 Mar 1977, 25 pp. (German). (Germany). CODEN: GWXXBX. CLASS: IC: C09B039-00. PRIORITY: GB 75-37158 9 Sep 1975. DOCUMENT TYPE: Patent CA Section: 40 (Dyes, Fluorescent Whitening Agents, and Photosensitizers) Section cross-reference(s): 75 Dichroic azo dyes I [R = H and R1 = Me, or (RR1) = (CH2)3 or COCH2CH2] and II [62607-16-3] were prepd. 17557-67-4 and 121-66-4 are also in the experiment., esp. for use in liq. crystal display devices. The dyes were prepd. by coupling diazotized 2-amino-5-nitrothiazole [121-66-4] with 1,2,3,4-tetrahydro-1-methylquinoline [491-34-9], julolidine [479-59-4], or 1-ketojulolidine (III) [51315-09-4], or diazotized 2-amino-6-(methylsulfonyl)benzothiazole [17557-67-4] with III. .

Problems and improvements in the synthesis of julolidines

Problems and improvements in the synthesis of julolidines. Katayama, Hajime; Ohgoshi, Mitsuko; Tanaka, Nobuyuki; Abe, Eiichi; Kaneko, Kimiyoshi (Niigata Coll. Pharm., Niigata 950-21, Japan). 89316-67-6 and 479-59-4 are also occured in this study. Niigata Yakka Daigaku Kenkyu Hokoku, 3, 27-36 (English) 1983. CODEN: NYDHDC. ISSN: 0285-3663. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Julolidines I (Rn = H, 8-, 9-Me, 9-Pr-10-Me, Me2) were prepd. from 1,2,3,4-tetrahydroquinolines and anilines. E.g., 1,2,3,4-tetrahydroquinoline was N-alkylated with Cl(CH2)3OH in MeCN contg. KI, Na2CO3, and 18-crown at 95° 40 h to give 70.3% alc. II which was converted to II.HCl. This underwent Friedel-Crafts cyclization at 185° with NH4Cl and AlCl3 in 16 h to give 58% I (R = H). Also, N-alkylating 4-MeC6H4NH2 with Cl(CH2)3OH gave 77% 4-MeC6H4N[(CH2)3OH]2 which, with 48% HBr, was converted to 89.5% 4-MeC6H4[(CH2)3Br]2. This was heated 2 h at 190° in o-Cl2C6H4 to give 31.1% I (R = 9-Me). .