Hydrochloric Acid → 4-(Hydroximinomethyl)cinnoline

HRID 255853Notes

Reaction equation

HRID 255853 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.Cl.[N:13](OCCCC)=[O:14]>C(O)C>[N:13](=[CH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1)[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 26843Cinnoline, 4-methyl-

Product 1

HCID 1363937104-(Hydroximinomethyl)cinnoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 1.44 g of 27A in 3 ml of absolute ethanol was added drop-by-drop over 3 minutes to 3.4 ml of stirred absolute ethanol containing 0.9 g of anhydrous hydrogen chloride, at 0° C. The resulting mixture was stirred for 30 minutes, then a solution of 1.03 g of butyl nitrite in 2 ml of absolute ethanol was added drop-by-drop over 3 minutes at 0° C. The mixture was stirred for 30 minutes at 0° C., for 4 hours at room temperature, then stored in a refrigerator overnight. A precipitated solid was collected, washed with a small amount of water, mixed with a saturated potassium bicarbonate solution, and filtered. Recrystallization from water gave 4-(hydroximinomethyl)cinnoline (27B), as a solid, m.p.: 223° C. (with decomposition).

Workup

  1. stirringThe mixture was stirred for 30 minutes at 0° C., for 4 hours at room temperature
  2. customstored in a refrigerator overnight
  3. customA precipitated solid was collected
  4. washwashed with a small amount of water
  5. additionmixed with a saturated potassium bicarbonate solution
  6. filtrationfiltered
  7. customRecrystallization from water

Sources & evidence

ORD record
ord-ba1e898e4ef54c7482039a0a44f463ab
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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