Methanol → 2-Amino-5-bromo-alpha-(2-pyridyl)benzyl alcohol

HRID 1801

反応式

HRID 1801 の反応式
NC1C=CC(Br)=CC=1C1C([C:15]([C:17]2[C:22]([C:23]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:24]=3[NH2:30])=[CH:21][CH:20]=[CH:19][N:18]=2)=O)=NC=CC=1.[BH4-].[Na+].C[OH:34]>>[NH2:30][C:24]1[CH:25]=[CH:26][C:27]([Br:29])=[CH:28][C:23]=1[CH:22]([OH:34])[C:17]1[CH:15]=[CH:21][CH:20]=[CH:19][N:18]=1

参加物

4

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 699474122-Amino-5-bromophenyl-2-pyridylketone

生成物 1

HCID 129155002-Amino-5-bromo-alpha-(2-pyridyl)benzyl alcohol

実験手順

In 100 ml of methanol was dissolved 10 g of 2-amino-5-bromophenyl-2-pyridylketone. To the solution was added 1.7 g of sodium borohydride and stirred for 30 minutes. The solvent methanol was evaporated off under reduced pressure. The residue was treated with an aqueous solution of hydrochloric acid. The decomposed residue was then neutralized with 200 ml of a sodium bicarbonate aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol (9.0 g) as prisms, m.p. 104°-105° C.

後処理

  1. customThe solvent methanol was evaporated off under reduced pressure
  2. additionThe residue was treated with an aqueous solution of hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-b73af90813ea458ca97a1404afcbed16
出典データセット
uspto-grants-1998_03
特許番号
US05726306

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