Hydrochloric Acid → 8-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

HRID 920920Notes

Reaction equation

HRID 920920 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[CH2:42][CH2:43]O.[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[NH:53][N:52]=[CH:51]2.Cl>C1COCC1>[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[N:53]([CH2:43][CH2:42][C:33]1[CH:34]=[CH:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:32]=1)[N:52]=[CH:51]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5462977Diethyl azodicarboxylateHCID 713076628-Chloro-1(2H)-phthalazinone

Product 1

HCID 717436398-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (9.00 g, 34.3 mmol) in THF (100 mL), DEAD (5.44 mL, 34.3 mmol) was added at 0° C. After stirring for 15 min, 2-(quinolin-2-yl)ethanol from Example a1 (2.97 g, 17.17 mmol) was added. After another 15 min, 8-chlorophthalazin-1(2H)-one (3.1 g, 17.17 mmol) was added. The mixture was stirred overnight at room temperature; LC-MS indicated complete conversion to the product. 1 N HCl was added (pH=4). The mixture was extracted with EtOAc (3×50 mL), the EtOAc layers were discarded. The aqueous layer was neutralized by aq.NaHCO3 and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was suspended in EtOAc. The solid was filtered through a Büchner funnel. The purity of the title product was 95%.

Workup

  1. waitAfter another 15 min
  2. stirringThe mixture was stirred overnight at room temperature
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. extractionNaHCO3 and extracted with ethyl acetate (3×500 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe solid was filtered through a Büchner funnel

Sources & evidence

ORD record
ord-a7ca25ba64f14cc09726916b3f7c2876
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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