(4-Amino-6-chloropyridin-3-yl)methanol → 4-Amino-6-chloropyridine-3-carbaldehyde

HRID 715090Notes

Reaction equation

HRID 715090 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9][OH:10]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:3]([CH:9]=[O:10])=[CH:4][N:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 1

HCID 21073390(4-Amino-6-chloropyridin-3-yl)methanol

Product 1

HCID 454801984-Amino-6-chloropyridine-3-carbaldehydeYield 73%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (4-amino-6-chloropyridin-3-yl)methanol (10 g, 63.3 mmol) in DCM (150 mL) with activated manganese dioxide (38 g, 443 mmol) and stir at RT overnight. Remove solids via filtration, concentrate the filtrate and purify by silica gel chromatography to afford the title compound (7.2 g, 73%). 1H NMR (400 MHz, DMSO-d6): δ 9.88 (s, 1H), 8.44 (s, 1H), 7.84 (s, 2H), 6.73 (s, 1H); MS (ESI) m/z: 157.0 (M+H+).

Workup

  1. customRemove solids
  2. filtrationvia filtration
  3. concentrationconcentrate the filtrate
  4. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-f7ce3750fcc64e6e96ee9ba6ed5404c5
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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