Water → 6-Aminoquinoline-5-carbohydrazide

HRID 1387408Notes

Reaction equation

HRID 1387408 reaction equation
[N:1](=[C:3]1[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[NH:5]C1=O)[N:12]=[CH:11][CH:10]=[CH:9]3)[NH2:2].NN.[OH2:19]>>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]=1[C:3]([NH:1][NH2:2])=[O:19]

Participants

4

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 178514317HCID 178514317, compound

Product 1

HCID 451169886-Aminoquinoline-5-carbohydrazide

Conditions

Temperature
145 °C

Procedure

1-Hydrazono-1,3-dihydro-pyrrolo[3,2-f]quinoline-2-one (1.07 g, 5.05 mmol) was combined with 6.0 mL of anhydrous hydrazine and 5.0 mL of water in a 100 mL flask (oversize to allow for foaming) and heated at reflux (145° C. oil bath) under a condenser and nitrogen atmosphere, with stirring. After 4.5 hr, analytical HPLC showed that all of the hydrazone had been consumed. The reaction was cooled, diluted with 75 mL of water, and filtered to give 0.45 g (air dried) of 6-aminoquinoline-5-carboxylic acid hydrazide as an olive brown solid. Mass spectrum (negative ion electrospray): m/z=215 (100%). NMR (DMSO-d6): δ3.64 (s, 2H), 4.22 (s, 2H), 5.66 (s, 2H), 7.25 (d, 1H, J=9.1 Hz), 7.34 (m, 1H), 7.65 (d, 1H, J=9 Hz), 8.34 (d, 1H, J=8.5 Hz), 8.50 (s, 1H), 9.27 (s, 1H).

Workup

  1. temperature(oversize to allow for foaming) and heated
  2. customhad been consumed
  3. temperatureThe reaction was cooled
  4. additiondiluted with 75 mL of water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0e451ad023b640eea48bc590390cceb3
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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