Ethanol → (4-Aminophenyl)(2-methylindolizin-3-yl)methanone

HRID 535470Notes

Reaction equation

HRID 535470 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5]2.O.C(O)C>[Zn].C(O)(=O)C>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([C:10]2[N:9]3[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]3)=[CH:3][C:2]=2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 23993764(2-Methylindolizin-3-yl)(4-nitrophenyl)methanone

Product 1

HCID 66653274(4-Aminophenyl)(2-methylindolizin-3-yl)methanoneYield 81.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

5.66 g (86.57 mmol) of zinc and 20.63 ml (360.71 mmol) of glacial acetic acid are added to 6.74 g (24.05 mmol) of (2-methylindolizin-3-yl)(4-nitrophenyl)methanone in 120 ml of a 2/1 mixture of water and ethanol. The reaction medium is heated at 80° C. for 4 hours. 0.57 g (8.7 mmol) of zinc and 2.06 ml of glacial acetic acid are added. Refluxing is maintained for 1 hour. At ambient temperature, the reaction medium is filtered off. The residue obtained is rinsed with ethyl acetate and with methyl THF. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, and then concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 4.9 g of a yellow solid are obtained.

Workup

  1. temperatureRefluxing
  2. temperatureis maintained for 1 hour
  3. filtrationAt ambient temperature, the reaction medium is filtered off
  4. customThe residue obtained
  5. washis rinsed with ethyl acetate and with methyl THF
  6. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  7. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-1e2c03663d6d4639874783a094d84a6a
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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