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

HRID 1419056Notes

Reaction equation

HRID 1419056 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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 hyrochloric acid. The decomposed residue was then neutralized with 200 ml of a sodium bicarbonate aqeous 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.

Workup

  1. customThe solvent methanol was evaporated off under reduced pressure
  2. additionThe residue was treated with an aqueous solution of hyrochloric 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)

Sources & evidence

ORD record
ord-c19c0ce7d18c4ad1b1ef49d01f6257cc
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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