Water → 5-(4-Methoxyanilino)-1,8-naphthyridin-2-ylmethanol

HRID 128632

반응식

HRID 128632 반응식
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8]2[CH:17]=[CH:16][N:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([C:18](OC)=[O:19])=[N:13]3)=[CH:5][CH:4]=1.C([BH-](CC)CC)C.[Li+].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8]2[CH:17]=[CH:16][N:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([CH2:18][OH:19])=[N:13]3)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 19374293Methyl 5-(4-methoxyanilino)-1,8-naphthyridine-2-carboxylateHCID 23664628Lithiumtriethylborohydride2회

생성물 1

HCID 193742625-(4-Methoxyanilino)-1,8-naphthyridin-2-ylmethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A mixture of methyl 5-(4-methoxyanilino)-1,8-naphthyridine-2-carboxylate (1.0 g) and dry THF (100 ml) was stirred at 0° C. while lithium triethylborohydride (a 1M solution in THF, 6.5 ml) was added over 10 minutes. After stirring at 0° C. for 1 hour further lithium triethylborohydride solution (3 ml) was added. The mixture was stirred for a further 1.5 hours at 0° C. Water (100 ml) was added cautiously and the mixture was extracted with ethyl acetate. The ethyl acetate extract was extracted with 0.5M hydrochloric acid. The acid extract was washed with ethyl acetate, basified with sodium bicarbonate and extracted with dichloromethane:methanol (3:1) (2×200 ml) to give a residue which was triturated with methanol and filtered. The solid obtained was triturated with ethyl acetate and filtered to give 5-(4-methoxyanilino)-1,8-naphthyridin-2-ylmethanol, m.p. 275°-281° C.

후처리

  1. additionwas added over 10 minutes
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. extractionwas extracted with 0.5M hydrochloric acid
  6. extractionThe acid extract
  7. washwas washed with ethyl acetate
  8. extractionextracted with dichloromethane:methanol (3:1) (2×200 ml)
  9. customto give a residue which
  10. customwas triturated with methanol
  11. filtrationfiltered
  12. customThe solid obtained
  13. customwas triturated with ethyl acetate
  14. filtrationfiltered

출처 및 근거

ORD 기록
ord-849c8c1917134b6f811ca33b593a73ef
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464781

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