Ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate → HCID 13055757, compound

A suspension of 19.71 g (73 mmol) of ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate in 350 ml of freshly distilled anhydrous tetrahydrofuran was stirred under a nitrogen atmosphere at room temperature and 3.33 g (88 mmol) of lithium aluminum hydride were added thereto in portions over 3 hours. The mixture was stirred for 4 hours and excess hydride was destroyed by dropwise addition of wet tetrahydrofuran followed by water. The mixture was poured into 1.5 liters of water and the mixture was extracted with 500 ml of a chloroform-methanol mixture. The mixture was filtered through a celite pad and the aqueous phase was extracted again with a chloroform-methanol mixture. The combined organic phases were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue was triturated with ethyl acetate, filtered, washed with ethyl acetate and dried under reduced pressure over P2O5 to obtain 14.87 g (89% yield) of 5-methoxy-imidazo[1,2-a]quinoline-2-methanol as a white crystalline solid melting at 173°-175° C.

1. stirringThe mixture was stirred for 4 hours
2. customexcess hydride was destroyed by dropwise addition of wet tetrahydrofuran
3. additionThe mixture was poured into 1.5 liters of water
4. extractionthe mixture was extracted with 500 ml of a chloroform-methanol mixture
5. filtrationThe mixture was filtered through a celite pad
6. extractionthe aqueous phase was extracted again with a chloroform-methanol mixture
7. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
8. customevaporated to dryness under reduced pressure
9. customThe residue was triturated with ethyl acetate
10. filtrationfiltered
11. washwashed with ethyl acetate
12. dry with materialdried under reduced pressure over P2O5

ORD record

ord-faf7a24c59de4f2788d8691028865a32

Source dataset

uspto-grants-1983_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04387098