HCID 43152698, compound → HCID 57900557, compound

HRID 1672359Notes

Reaction equation

HRID 1672359 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-])=O)=[CH:4][CH:3]=1>CO.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([NH2:14])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 43152698HCID 43152698, compound

Product 1

HCID 57900557HCID 57900557, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room-temperature solution containing 6-chloro-3-nitro-N-(pentan-3-yl)pyridin-2-amine (1.8 g, 7.4 mmol) in MeOH (10 mL) and EtOAc (10 mL) was added SnCl2 dihydrate (10.0 g, 44.3 mmol). After 3 h, the reaction mixture was concentrated in vacuo and then re-dissolved in EtOAc and water. After stirring overnight, the layers were separated and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (25%-50% EtOAc/Hexanes) provided the title compound as a white solid (940 mg, 57%). m/z=223.2 (M+H)+

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionre-dissolved in EtOAc
  3. customthe layers were separated
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0d6ca3ec280463e96fdea1a46cda34e
Source dataset
uspto-grants-2011_08
Patent number
US07998976B2

Reaction notes

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