Sodium Hydroxide → HCID 69859166, compound

HRID 1456319Notes

Reaction equation

HRID 1456319 reaction equation
[N+:1]([C:4]1[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H].[OH-].[Na+]>C(O)C.Cl>[C:13]1([CH3:16])[CH:12]=[CH:11][C:10]([C@H:5]2[C@@H:4]([NH2:1])[CH2:9][CH2:8][CH2:7][NH:6]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11241348HCID 11241348, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69859166HCID 69859166, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of 3-nitro-2-p-tolylpyridine (5.0 g) in ethanol (200 ml) and concentrated hydrochloric acid (15 ml) was hydrogenated over pre-reduced platinum oxide (1.5 g) at 23°1 atm until hydrogen uptake was complete (~3 lh). The mixture was filtered through hyflo washing the pad of hyflo with water then the filtrate was evaporated in vacuo. Recrystallisation from isopropanol water gave a cream solid. The solid was treated with 2N sodium hydroxide solution and extracted with dichloromethane (5×200 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound as an orange-brown oil which partially crystallised on standing (2.20 g).

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. washwashing the pad of hyflo with water
  3. customthe filtrate was evaporated in vacuo
  4. customRecrystallisation from isopropanol water
  5. customgave a cream solid
  6. extractionextracted with dichloromethane (5×200 ml)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-2a46ad45f7984c92951b5851a3a48050
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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