Hydrochloric Acid → ethyl-3-cyanoethyl-4-oxo-3-H-phthalazin-1-ylacetate

HRID 1607979Notes

Reaction equation

HRID 1607979 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1)[CH3:2].CC(C)([O-])C.[K+].Cl[CH2:25][CH2:26][C:27]#[N:28].Cl>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:25][CH2:26][C:27]#[N:28])[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 109633-ChloropropionitrileHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14519537ethyl-3-cyanoethyl-4-oxo-3-H-phthalazin-1-ylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl-4-oxo-3-H-phthalazin-1-ylacetate (10.91 g) and dry potassium t-butoxide (5.90 g) in dimethylformamide (50 ml) was added 3-chloropropionitrile (4.92 g) and the resulting solution was stirred for 30 minutes. The solution was then poured onto ice-water (300 ml); sufficient 10% HCl was added to adjust the pH of the resulting mixture to about 4.0 and the precipitated solid was collected and crystallized from methanol (yield: 7.64 g; m.p. 125°-126° C.).

Workup

  1. additionThe solution was then poured onto ice-water (300 ml)
  2. customthe precipitated solid was collected
  3. customcrystallized from methanol (yield: 7.64 g; m.p. 125°-126° C.)

Sources & evidence

ORD record
ord-87dd6bd3f26c4763822bbcd631419ff8
Source dataset
uspto-grants-1989_09
Patent number
US04868301

Reaction notes

Loading…