(3-Amino-6-chloropyridin-2-yl)methanol → 3-Amino-6-chloropyridine-2-carbaldehyde

HRID 475328Notes

Reaction equation

HRID 475328 reaction equation
[NH2:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19353056(3-Amino-6-chloropyridin-2-yl)methanol

Product 1

HCID 574611393-Amino-6-chloropyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

(3-amino-6-chloro-pyridin-2-yl)-methanol (998 mg, 4.0 mmol) is taken up in DCM and combined with MnO2 (697 mg, 8.0 mmol). After 24 h another 2 eq. MnO2 are added and the mixture is stirred for further 24 h at RT. Then the reaction mixture is filtered through Celite®, the solvent is removed and 3-amino-6-chloro-pyridine-2-carbaldehyde (HPLC-MS: tRet.=1.88 min, MS(M+H)+=157; method AFEC) is obtained.

Workup

  1. filtrationThen the reaction mixture is filtered through Celite®
  2. customthe solvent is removed

Sources & evidence

ORD record
ord-52859f8862c1431c8d94750591a07f6f
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

Loading…