Hydrochloric Acid → HCID 19379704, compound

Methyl 1,2-dihydro-l-methyl-2-oxo-4-quinoline acetate (2.35 g, 10.16 mmol) was dissolved in dry tetrahydrofuran (50 ml) and sodium borohydride (1.92 g, 50.8 mmol) was added thereto. The mixture was refluxed. Under the same conditions, methanol (19 ml) was slowly added dropwise thereto (over 1 hour) and the mixture was refluxed for 1 hour. To the reaction mixture was acidified (pH about 2) with 2N-hydrochloric acid. The solvent was distilled off and water (300 ml) was poured to the residue. The mixture was extracted with chloroform (300 ml×3). The organic layer was separated, dried (over magnesium sulfate) and the solvent was distilled off. The residue was crystallized with ether to give the entitled compound (1.80 g) as white crystals (yield 87.2%, mp 149°-150 ° C. (chloroform--hexane)).

1. temperatureThe mixture was refluxed
2. temperature(over 1 hour) and the mixture was refluxed for 1 hour
3. distillationThe solvent was distilled off
4. additionwater (300 ml) was poured to the residue
5. extractionThe mixture was extracted with chloroform (300 ml×3)
6. customThe organic layer was separated
7. dry with materialdried (over magnesium sulfate)
8. distillationthe solvent was distilled off
9. customThe residue was crystallized with ether

ORD record

ord-e15fc534d7d542d59d5976b938d831b8

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05457099