6-Hydroxyquinoline → HCID 11573719, compound

A solution of quinolin-6-ol (0.29 g., 2 mmol) in dry dimethylformamide (3 ml) was added to a stirred suspension of sodium hydride (0.048 g., 2 mmol) in dry dimethylformamide (2 ml) at −10° C. during 5 min. The reaction mixture was stirred for ½ hours. Then 3-bromo-phenyl isocyanate (0.475 g., 2.4 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 1 hr. during which the temperature was allowed to rise to room temperature (21° C.). The reaction mixture was quenched with water (0.2 ml), diluted with water (2 ml), extracted with ethyl acetate (2×5 ml) and dried over sodium sulphate. The combined fractions of ethyl acetate were concentrated under vaccum. The residue was washed with methanol (2×2 ml) to give 1d; yield: 0.35 g. (51.01%), m.p. 260° C., C16H11BrN2O2; 1H NMR δ ppm (pyridine d5): 7.09-7.58 (m, 9H), 8.28 (bs, 2H), 9.58 (bs, 1H); IR vmax (KBr) (cm−1). 522, 645, 743, 782, 877, 928, 992, 1069, 1227, 1286, 1406, 1470, 1581, 1637, 1875, 1946, 2374, 3290, 3753, 3872, 3952.

1. stirringStirring
2. waitwas continued for additional 1 hr
3. customto rise to room temperature
4. custom(21° C.)
5. customThe reaction mixture was quenched with water (0.2 ml)
6. additiondiluted with water (2 ml)
7. extractionextracted with ethyl acetate (2×5 ml)
8. dry with materialdried over sodium sulphate
9. concentrationThe combined fractions of ethyl acetate were concentrated under vaccum
10. washThe residue was washed with methanol (2×2 ml)

ORD record

ord-81681b09f0fc4550801580fe5f0f8824

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655801B2