Sodium Carbonate → HCID 67078112, compound

Temperature

75 °C

A mixture of 4-hydrazino-2-methyl-quinolin-8-ol (21 mg, 0.11 mmol) and 4-ethoxy-1,1,1-trifluoro-but-3-en-2-one (16 μL, 0.11 mmol) in ethanol (0.5 mL) was heated to 75° C. for 30 min. The solvent was than removed in vacuo and the residue was redissolved in acetic acid (0.5 mL). After the addition of concentrated H2SO4 (20 μL) and stirring for 1 h at 100° C., the reaction mixture was cooled to room temperature and a mixture of Na2CO3 (0.40 mg, 3.8 mmol) in water (1 mL) was added. The reaction mixture was then concentrated in vacuo and the residue was partitioned between DCM (10 mL) and water (5 mL). The pH of the aqueous layer was adjusted to 10 by the addition of saturated aqueous NH3 solution and the aqueous layer was extracted with DCM (1×320 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS (m/z): 294.2 [M+H+].

1. customthan removed in vacuo
2. dissolutionthe residue was redissolved in acetic acid (0.5 mL)
3. additionAfter the addition of concentrated H2SO4 (20 μL)
4. temperaturethe reaction mixture was cooled to room temperature
5. additionwas added
6. concentrationThe reaction mixture was then concentrated in vacuo
7. customthe residue was partitioned between DCM (10 mL) and water (5 mL)
8. additionThe pH of the aqueous layer was adjusted to 10 by the addition of saturated aqueous NH3 solution
9. extractionthe aqueous layer was extracted with DCM (1×320 mL)
10. dry with materialThe combined organic layers were dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-bf60955b87a440469b2ba9377188e66e

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410134B2