Acetic Acid → 2-Amino-5-bromo-3-(hydroxymethyl)pyridine
Reaction equation
[Br:1]Br.Cl.O=[C:5]1[NH:14][C:13]2[N:12]=CC(/C=C/C(O)=O)=CC=2[CH2:7][CH2:6]1.[C:20]([OH:23])(=O)[CH3:21]>>[NH2:12][C:13]1[C:21]([CH2:20][OH:23])=[CH:7][C:6]([Br:1])=[CH:5][N:14]=1Participants
Procedure
Bromine (8.4 mL, 189.4 mmol) was added dropwise over 1 hour to a solution of 2-amino-3-(hydroxymethyl)pyridine (19.6 g, 157.8 mmol; which may be prepared as described in D1, Step 1) in acetic acid (350 mL) at room temperature. The reaction mixture was then stirred overnight. After concentration to dryness, the residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 mL). The aqueous layer was separated and extracted with ethyl acetate (2×200 mL). The combined organic phases were washed with a saturated solution of sodium chloride (200 mL), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in pentane, the title product was obtained as a yellow solid (27.0 g, 84%).
Workup
- concentrationAfter concentration to dryness
- customthe residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 mL)
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate (2×200 mL)
- washThe combined organic phases were washed with a saturated solution of sodium chloride (200 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-e8593c3232864a649d120bd71b83e92e
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051321B2
Reaction notes
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