Hydrazine → HCID 178514317, compound

HRID 1387407Notes

Reaction equation

HRID 1387407 reaction equation
[C:1]1(=O)[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3.[NH2:16][NH2:17]>O>[N:16](=[C:1]1[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3)[NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

Product 1

HCID 178514317HCID 178514317, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3-H-Pyrrolo[3,2-f]quinoline-1,2-dione (3.89 g, 19.6 mmol) was combined with 12.0 mL of anhydrous hydrazine and 10.25 mL of water and heated at 100° C. under a condenser and nitrogen atmosphere, with stirring, for 1 hr. The reaction occasionally foamed into the condenser and heat was removed as needed to allow foaming to subside. The reaction was cooled and poured into 200 mL of water. The product was collected by filtration and dried under vacuum at 55° C. to give 2.86 g (69%) of 1-hydrazono-1,3-dihydropyrrolo[3,2-f]quinoline-2-one as a brown solid. Mass spectrum (positive ion electrospray): m/z=213. NMR (DMSO-d6): δ7.37 (d, J=8.8 Hz, 1H), 7.47 (dd, J=8.4, 4.2 Hz, 1H), 7.81 (d, J=8.8 Hz, 1H), 8.71 (dd, J=4.2, 1.6 Hz, 1H), 8.80 (d, J=8.4 Hz, 1H), 9.90 (br d, J=14.7 Hz, 1H), 10.89 (br d, J=14.7 Hz, 1H), 10.95 (br s, 1H).

Workup

  1. customThe reaction
  2. temperatureheat
  3. customwas removed
  4. temperatureThe reaction was cooled
  5. additionpoured into 200 mL of water
  6. filtrationThe product was collected by filtration
  7. customdried under vacuum at 55° C.

Sources & evidence

ORD record
ord-1b2e028b5961469288dc8502355d3df2
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

Loading…