Bromine → 2-Amino-5-bromo-3-(hydroxymethyl)pyridine

HRID 225889Notes

Reaction equation

HRID 225889 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:10]Br>CC(O)=O>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridineYield 75.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-amino-3-(hydroxymethyl)pyridine (15.0 g, 121 mmole) in HOAc (300 mL) at RT was added bromine (6.2 mL, 121 mmole) dropwise over 1 hr. A suspension formed after approximately 15 min. After the addition, the reaction was stirred for an additional 1 hr, then was concentrated under vacuum. The residue was taken up in 1.0 M Na2CO3 (500 mL), and the solution was extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The resulting residue was triturated with a small volume of petroleum ether, filtered and dried under vacuum to give the title compound (18.45 g, 75%) as a beige solid: LCMS (ES) m/e 203.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 7.89 (d, J=2.3 Hz, 1 H), 7.52 (s, 1 H), 5.92 (br s, 2 H), 5.29 (br s, 1 H), 4.30 (s, 2 H).

Workup

  1. customA suspension formed after approximately 15 min
  2. additionAfter the addition
  3. concentrationwas concentrated under vacuum
  4. extractionthe solution was extracted with ethyl acetate (2×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was triturated with a small volume of petroleum ether
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-303f2d2c64fc40a7b51fb9d9377e9e63
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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