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

HRID 1361931Notes

Reaction equation

HRID 1361931 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>[BrH:10].[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 441196112-Amino-5-bromo-3-(hydroxymethyl)pyridine hydrobromideYield 161.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-amino-3-(hydroxymethyl)pyridine (156 g, 1.257 mole) in HOAc (2.5 L) at ambient temperature was added bromine (64.1 mL, 1.257 mole) dropwise over 1 hr. A suspension began to form during the addition. An exotherm to 36° C. was controlled with an ice bath. After the addition, the reaction mixture was stirred at ambient temperature overnight. The yellow precipitate was filtered, washed with ether and air-dried to give the title compound (289 g, 81%): MS (ES) m/e 203.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6, free base) δ 7.89 (d, J=2.3 Hz, 1H), 7.52 (s, 1H), 5.92 (br s, 2H), 5.29 (br s, 1H), 4.30 (s, 2H).

Workup

  1. customto form during the addition
  2. customAn exotherm to 36° C. was controlled with an ice bath
  3. additionAfter the addition
  4. filtrationThe yellow precipitate was filtered
  5. washwashed with ether
  6. customair-dried

Sources & evidence

ORD record
ord-bccc7f8030d34834858e52c4e34f6dff
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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