Hydrochloric Acid → HCID 86720686, compound

HRID 2284827Notes

Reaction equation

HRID 2284827 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21]CC2CC2)[CH:12]=1)[OH:10].Cl.[OH-].[Na+]>O>[Cl:26][C:6]1[CH:5]=[N+:4]([O-:27])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([OH:21])[CH:12]=1)[OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 71092687HCID 71092687, compound

Product 1

HCID 86720686HCID 86720686, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (5 g, 11.90 mmol) was added to 100 mL of 37% HCl and stirred at room temperature for about 3 min., to obtain a yellow solution. After stirring for further 3 min. the solution was poured into a solution of NaOH (48 g) in water (500 mL). The red solution was added with 1 M HCl to pH 1. The brown solid was filtered, washed with water and triturated with hot EtOH (50 mL). After stirring at r.t. for 1 h the solid was filtered, washed with EtOH and dried under vacuum at 40 C yielding 2.4 of the title compound.

Workup

  1. customto obtain a yellow solution
  2. stirringAfter stirring for further 3 min. the solution
  3. filtrationThe brown solid was filtered
  4. washwashed with water
  5. customtriturated with hot EtOH (50 mL)
  6. stirringAfter stirring at r.t. for 1 h the solid
  7. filtrationwas filtered
  8. washwashed with EtOH
  9. customdried under vacuum at 40 C

Sources & evidence

ORD record
ord-c2f106b9aba343adaad917a3511cfd97
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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