Trifluoroacetic acid → 2-Amino-4-chloropyridine-3-carbaldehyde

HRID 1724873Notes

Reaction equation

HRID 1724873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8]C(=O)OC(C)(C)C)[C:3]=1[CH:16]=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:4]1[N:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46204204tert-Butyl 4-chloro-3-formylpyridin-2-ylcarbamate

Product 1

HCID 462035412-Amino-4-chloropyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tert-butyl 4-chloro-3-formylpyridin-2-ylcarbamate (1.6 g, 6.2 mmol) in anhydrous CH2Cl2 (50 mL) under N2 atmosphere. Add dropwise trifluoroacetic acid (2.4 mL, 31.0 mmol) to the reaction mixture and stir at room temperature overnight. Add saturated aq. sodium carbonate (50 mL) to the reaction mixture, separate the organic layer, extract the aq. layer with CH2Cl2 (2×20 mL) and dry with MgSO4. Filter and concentrate under reduced pressure to afford the title product as a yellow solid.

Workup

  1. customAdd saturated aq. sodium carbonate (50 mL) to the reaction mixture, separate the organic layer
  2. extractionextract the aq. layer with CH2Cl2 (2×20 mL)
  3. dry with materialdry with MgSO4
  4. filtrationFilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-5d6e7cc38d264582a06567993077d696
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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