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

HRID 128632

反応式

HRID 128632 の反応式
[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

参加物

5

反応物 3

HCID 962WaterHCID 19374293Methyl 5-(4-methoxyanilino)-1,8-naphthyridine-2-carboxylateHCID 23664628Lithiumtriethylborohydride2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-849c8c1917134b6f811ca33b593a73ef
出典データセット
uspto-grants-1995_11
特許番号
US05464781

関連ノート

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