Acetic Anhydride → 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 888098Notes

Reaction equation

HRID 888098 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].[C:21](OC(=O)C)(=[O:23])[CH3:22]>O>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]([C:21](=[O:23])[CH3:22])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 590215001-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline (1.08 g) was heated at reflux in 10 ml of acetic anhydride for 2 h, cooled to RT, diluted with water (100 ml), neutralized to pH7 with NaHCO3 (solid) and extracted with EtOAc. The organic portion was washed with brine, removal of the solvents afforded 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine, removal of the solvents

Sources & evidence

ORD record
ord-a3383cffbda74b7f8fa307de9b1e50ee
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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