Pyridine → 2-Acetylamino-5-nitroquinoline

HRID 2054946Notes

Reaction equation

HRID 2054946 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C([O-])(O)=O.[Na+]>[Na+].[Cl-]>[C:21]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 219489145-Nitroquinolin-2-amine

Product 1

HCID 219488732-Acetylamino-5-nitroquinoline

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

360 mg (1.9 mmol) of 2-amino-5-nitroquinoline is stirred with 4 ml (50 mmol) of pyridine and 2 ml (21 mmol) of acetic anhydride for 15 hours at room temperature. The batch is poured into saturated NaHCO3 solution, stirred for 30 minutes, diluted with saturated NaCl solution and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated by evaporation: 410 mg of a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-49ce681d4def4f9aad45f61e6336ba71
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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