3-Chloroaniline → HCID 178526355, compound

HRID 1405997Notes

Reaction equation

HRID 1405997 reaction equation
[F:1][C:2]1[C:3]([C:8](Cl)=[N:9][OH:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16]>O1CCOCC1>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:8](=[N:9][OH:10])[C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 136359764HCID 136359764, compound

Product 1

HCID 178526355HCID 178526355, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-fluoro-N-hydroxypicolinimidoyl chloride 2 (1.35 g, 7.73 mmol) in 1,4-dioxane (15 mL) was added via cannula to a solution of 3-chloroaniline (4.5 mL, 43 mmol) in 1,4-dioxane (10 mL). After 12 h at rt, the r×n was added to EtOAc: H2CO (1:1). The organic layer was separated and washed with brine (30 mL), dried (MgSO4), filtered and concentrated to afford N-(3-chlorophenyl)-3-fluoro-N′-hydroxypicolinimidamide was taken through to the next step.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5fec16cce843400aa71214498896b640
Source dataset
uspto-grants-2014_12
Patent number
US08916584B2

Reaction notes

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