1-Chloro-4-phenylphthalazine → HCID 59427352, compound

HRID 1013692Notes

Reaction equation

HRID 1013692 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=3)=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1>CC(O)(C)C.C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([NH:37][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:35][CH:36]=3)=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 59427335HCID 59427335, compound

Product 1

HCID 59427352HCID 59427352, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 1-chloro-4-phenylphthalazine (0.082 g, 0.34 mmol) and 4-((7-methoxyquinolin-4-yl)methyl)benzenamine (0.090 g, 0.34 mmol) in tBuOH (2.5 mL) was heated to 105° C. in a resealable tube. After 3 hrs, the mixture was cooled to RT, diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic fraction was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography using 50-100% Hexanes:EtOAc to afford N-(4-((7-methoxyquinolin-4-yl)methyl)phenyl)-4-phenylphthalazin-1-amine as a light yellow solid. [email protected] min

Workup

  1. temperaturethe mixture was cooled to RT
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe organic fraction was dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-30af50557b1145eda4d6154104f96ccc
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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