HCID 14708119, compound → 2-Amino-5-chloropyridine-3-carbaldehyde

HRID 722357Notes

Reaction equation

HRID 722357 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[O:16])[C:5]([NH:8]C(=O)C(C)(C)C)=[N:6][CH:7]=1>Cl>[NH2:8][C:5]1[C:4]([CH:15]=[O:16])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

3

Reactant 1

HCID 14708119HCID 14708119, compound

Product 1

HCID 154285262-Amino-5-chloropyridine-3-carbaldehydeYield 121.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The product of Step 2 (2.7 g, 11 mmol) and 3 N HCl (50 mL) were heated at reflux for 2 hours. The reaction was allowed to cool to room temperature and was concentrated in vacuo yielding a light yellow solid (2.1 g). The solid was partitioned between ethyl acetate and 2.5 N NaOH solution. The ethyl acetate layer was dried over MgSO4 and concentrated in vacuo providing a solid (1.7 g). The solid was recrystallized from ethyl acetate to give the desired substituted pyridine as yellow needles (1.2 g, 68%): mp 176.1–177.3° C. 1H NMR (CDCl3/300 MHz) 9.80 (s, 1H), 8.21 (s, 1H), 7.75 (s, 1H), 6.75 (br s, 2H). Anal. Calc'd for C6H5N2OCl: C, 46.03; H, 3.22; N, 17.89 Found: C, 45.90; H, 3.24; N, 17.80.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-a7ab89f829084f79a8ff41435f2182db
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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