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

HRID 2219980Notes

Reaction equation

HRID 2219980 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:16](OC(=O)C)(=[O:18])[CH3:17].O>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[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:16](=[O:18])[CH3:17])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 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)ethanoneYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-4,4-dimethyl-7-nitroquinoline (Rami et al, WO 03/068749) (500 mg, 2.42 mmol), DMAP (5 mg) in pyridine (2 mL) was added acetic anhydride (0.46 mL, 4.9 mmol). The mixture was stirred at room temperature for 10 h, and then heated at 60° C. for 5 h. After cooling, the mixture was treated with water and extracted with EtOAc. The combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine, dried, and evaporated. The residue was purified by chromatography to give a light yellow solid (550 mg, 92%).

Workup

  1. temperatureheated at 60° C. for 5 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-3918ddff1ace42168345f296e94a4cec
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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