Potassium Carbonate → RS 14203

HRID 861971Notes

Reaction equation

HRID 861971 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C1(C)C=CC=CC=1>[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:12]2[C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11]2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 197007208-(3-Nitrophenyl) pyrido[2,3-d]pyridazin-5-one

Product 1

HCID 9808563RS 14203Yield 52.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
65 °C

Procedure

8-(3-nitrophenyl)-pyrido[2,3-d]pyridazin-5-one (5.12 g, 19.1 moles), sodium hydride (50% in oil, 1 g, 20.1 moles) were mixed in 100 mL of 1-methyl-2-pyrrolidone and the mixture heated to 65° C. In a separatory funnel, 4-picolyl chloride hydrochloride (4.5 g, 27.4 mmoles), 20 mL of saturated potassium carbonate and 75 mL of toluene are mixed. After separation, the toluene solution was added to the reaction mixture dropwise over the period of 1 hour. The reaction mixture was diluted with water (250 mL) and extracted twice with ethyl acetate (200 mL). After concentrating the organic fractions, methanol and hexanes (75 mL each) were added and the mixture allowed to stir at room temperature for 17 hours. The material was filtered and dried to yield 5.2 g of 6-(4-pyridylmethyl)-8-(3-nitro-phenyl)-pyrido[2,3-d]pyridazin-5-one.

Workup

  1. customAfter separation
  2. additionthe toluene solution was added to the reaction mixture dropwise over the period of 1 hour
  3. additionThe reaction mixture was diluted with water (250 mL)
  4. extractionextracted twice with ethyl acetate (200 mL)
  5. concentrationAfter concentrating the organic fractions, methanol and hexanes (75 mL each)
  6. additionwere added
  7. filtrationThe material was filtered
  8. customdried

Sources & evidence

ORD record
ord-790ee26f13044181a6017ad3805f8266
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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