Acetic Acid → HCID 66653091, compound

HRID 535462Notes

Reaction equation

C(O)(=O)C.[CH3:5][O:6][C:7]1[C:8]([CH3:27])=[C:9]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:17])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2.O>[Fe].C(O)C>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:9]2[N:10]3[C:15]([CH:14]=[CH:13][CH:12]=[CH:11]3)=[C:7]([O:6][CH3:5])[C:8]=2[CH3:27])=[O:17])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.93 g (34.46 mmol) of iron and 8.21 ml (143.57 mmol) of glacial acetic acid are added to 2.97 g (9.57 mmol) of (1-methoxy-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 3 hours. The reaction medium is extracted with ethyl acetate. 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. 2.58 g of a yellow solid are obtained.

Workup

extractionThe reaction medium is extracted with ethyl acetate
washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue obtained
customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record: ord-63c774f7b8c044d1b4c34fc4e10c82cc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859544B2

Reaction notes

Loading…