Water → HCID 178518943, compound

HRID 1514364Notes

Reaction equation

HRID 1514364 reaction equation
[C:1]1(=[O:11])[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3](=[O:10])[NH:2]1.O.O.[NH2:14]N>CCO>[C:1]1([OH:11])[N:14]=[N:2][C:3]([OH:10])=[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=12

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 729263,4-Pyridinedicarboximide

Product 1

HCID 178518943HCID 178518943, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To 2H-pyrrolo[3,4-c]pyridine-1,3-dione 1 (25.01 g, 169 mmol) dissolved in EtOH (250 mL) and H2O (250 mL) was added hydrazine hydrate (23 ml, 464 mmol). The solution was warmed to reflux and stirred for 1 h. After cooling to 40° C., the solution was brought to pH 4 with 5 N HCl whereupon precipitation of a light yellow solid occurred. After cooling to room temperature, the precipitate was filtered, washed with water, air dried for 2 h, and dried under high vacuum for 24 h at 40° C. to provide a quantitative yield of pyrido[3,4-d]pyridazine-1,4-diol 2. 1H NMR (d6-DMSO) δ 11.67 (bs, 2H), 9.33 (s, 1H), 9.02 (d, J=5.5 Hz, 1H), 7.89 (d, J=5.5 Hz, 1H).

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux
  3. customthe solution was brought to pH 4 with 5 N HCl whereupon precipitation of a light yellow solid
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was filtered
  6. washwashed with water, air
  7. customdried for 2 h
  8. customdried under high vacuum for 24 h at 40° C.

Sources & evidence

ORD record
ord-fc251ebdeba5439bb8a370c3be99791e
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

Loading…