Pyridine → 2-Acetylamino-5-nitroquinoline

HRID 2182664Notes

Reaction equation

HRID 2182664 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-3bf30cdc9706429fa4439e7afc01887c
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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