Water → 3-Bromo-5-chloropyridin-2-ol

HRID 1742054Notes

Reaction equation

HRID 1742054 reaction equation
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH2:10]>>[Br:8][C:7]1[C:2](=[O:10])[NH:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

3

Reactant 2

HCID 962WaterHCID 27639713-Bromo-5-chloropyridin-2-amine

Product 1

HCID 27267913-Bromo-5-chloropyridin-2-ol

Procedure

To a cooled (0° C.) solution of 2-amino-3-bromo-5-chloropyridine (100 g, 0.482 tool) in water (815 mL) and concentrated HC1 (130 mL) was added a solution of sodium nitrite (33.26 g, 0.482 tool) in water (272 mL). The resulting suspension was allowed to warm to room temperature and stir for 18 hours, at which point the solids were filtered, washed with carbon tetrachloride (2×50 mL), and dried in a vacuum oven (40° C.) to yield 75.1 g (74.8%) of gray-yellow so lid, m.p. 170°-173° C.: IR (mineral oil (Nujol (trademark ) ) 3111, 3041, 2947, 2850, 2722, 1814, 1696, 1663, 1643, 1585, 1527, 1462, 1377, 1302, 1234, 1171, 1153, 1123, 1106, 1040, 917, 896, 876, 839, 747, 726, 644, 635, 561, 539, 523, 410, 251, 235, 225, 220cm-1 ; 1H NMR (300 MHz, D6 -DMSO)δ 7.72 (d, 1H, J=2.2Hz) , 8.08 (d, 1H , J=2 . 2Hz ), 12.41 (br s, 1H); 13C NMR (DMSO) δ 110.88, 115.35, 134.08, 142.64, 157.56; exact mass calculated for C5H3NBrClO=206.9086. High resolution mass spec. 206.9093.

Workup

  1. concentrationconcentrated HC1 (130 mL)
  2. additionwas added a solution of sodium nitrite (33.26 g, 0.482 tool) in water (272 mL)
  3. filtrationwere filtered
  4. washwashed with carbon tetrachloride (2×50 mL)
  5. customdried in a vacuum oven (40° C.)
  6. customto yield 75.1 g (74.8%) of gray-yellow so lid, m.p. 170°-173° C.

Sources & evidence

ORD record
ord-8cdc5ac7e2fc4d1b9a763360afcb83d0
Source dataset
uspto-grants-1994_08
Patent number
US05336771

Reaction notes

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