Hydrochloric Acid → 6-Ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol

HRID 128626

반응식

HRID 128626 반응식
C([BH-](CC)CC)C.[Li+].[CH2:9]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[N:20][C:21]=1[CH3:22])[N:18]=[CH:17][C:16]([C:23](OCC)=[O:24])=[C:15]2[NH:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH3:10].Cl.O>C1COCC1>[CH2:9]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[N:20][C:21]=1[CH3:22])[N:18]=[CH:17][C:16]([CH2:23][OH:24])=[C:15]2[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH3:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9907935Ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylateHCID 23664628Lithiumtriethylborohydride2회

생성물 1

HCID 193742646-Ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium triethylborohydride (a 1M solution in THF, 47 ml) was added to a solution of ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate (4.5 g) in THF (150 ml) with stirring under nitrogen at 0°-10° C. The mixture was allowed to warm up to ambient temperature and stirred at this temperature for 18 hours. Further lithium triethylborohydride solution (15 ml) was added and the solution stirred at ambient temperature for 4 hours. The reaction mixture was cooled to 5° C. and then 5M hydrochloric acid (5 ml) was added carefully followed by water (50 ml). The organic layer was separated and the aqueous layer extracted with ether. The aqueous layer was basified with 5M sodium hydroxide solution and extracted into ethyl acetate. The residue, obtained from the ethyl acetate extracts, was purified by flash chromatography on silica, using dichloromethane/IMS (15/1) as the mobile phase, to give 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol, m.p. 193°-197° C.

후처리

  1. stirringstirred at this temperature for 18 hours
  2. stirringthe solution stirred at ambient temperature for 4 hours
  3. temperatureThe reaction mixture was cooled to 5° C.
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ether
  6. extractionextracted into ethyl acetate
  7. customThe residue, obtained from the ethyl acetate extracts
  8. customwas purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-560a97bfc68242c4acf9af5ea9b09111
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464781

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