Acetic Acid → 4-Phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 589091Notes

Reaction equation

HRID 589091 reaction equation
CO[N:3]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH2:8][CH2:7][CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:5]3[C:4]1=[O:21].C(O)C.C(O)(=O)C>>[C:15]1([CH:6]2[CH2:7][CH2:8][C:9]3[C:14]4=[C:13]([NH:3][C:4](=[O:21])[N:5]24)[CH:12]=[CH:11][CH:10]=3)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 904095351-Methoxy-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Product 1

HCID 904094724-Phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 85%

Procedure

A suspension of 1-methoxy-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (0.575 g, 2.05 mmol) in ethanol (35.9 mL, 615 mmol) was heated to dissolve residual solids and the resulting solution was cooled to room temperature. The solution was treated with acetic acid (0.233 mL, 4.10 mmol), degassed with nitrogen, treated with palladium catalyst (0.575 g, 100 wt %) (10% Pd on carbon, Degussa type) and hydrogenated for 17 h. The reaction mixture was filtered and the catalyst was washed with ethanol and methanol. The filtrate was then concentrated to give the desired product (0.436 g, 85%) as a racemic mixture that was used without further purification. LCMS calculated for C16H15N2O (M+H)+: m/z=251.1. found: 251.1.

Workup

  1. temperaturewas heated
  2. dissolutionto dissolve residual solids
  3. customdegassed with nitrogen
  4. additiontreated with palladium catalyst (0.575 g, 100 wt %) (10% Pd on carbon, Degussa type) and hydrogenated for 17 h
  5. filtrationThe reaction mixture was filtered
  6. washthe catalyst was washed with ethanol and methanol
  7. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-5cad8d6e1f5d4893a4e5382d1e9ce06b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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