Hydrochloric Acid → 4-Bromo-6-methylpyridin-3-ol

HRID 1807690Notes

Reaction equation

HRID 1807690 reaction equation
[Br:1][C:2]1[C:7]([O:8]COC)=[CH:6][N:5]=[C:4]([CH3:12])[CH:3]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[N:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580927874-Bromo-5-(methoxymethoxy)-2-methylpyridine

Product 1

HCID 580927194-Bromo-6-methylpyridin-3-olYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

920 mg (3.05 mmol) 4-bromo-5-methoxymethoxy-2-methyl-pyridine (Stage 40.5) were dissolved in 5 mL MeOH, HCl conc. (1 mL, 12 mmol) was added and the reaction mixture was stirred for 2 h at rt. While concentrating the mixture in vacuo, the title compound (as hydrochloride) crystallized. Filtration afforded 570 mg white crystals. 1H-NMR (d6-DMSO, 400 MHz): 8.19 (s, 1H), 8.04 (s, 1H), 2.53 (s, 3H).

Workup

  1. concentrationWhile concentrating the mixture in vacuo
  2. customthe title compound (as hydrochloride) crystallized
  3. filtrationFiltration

Sources & evidence

ORD record
ord-2ac0e1a9e42b4731b0061834b445d6ae
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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