5-Chloro-2-methylindole → 1-chloro-4-(5-chloro-2-methyl-1H-indol-3-yl)phthalazine

HRID 1453686Notes

Reaction equation

HRID 1453686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](Cl)=[N:15][N:14]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]=2[CH3:11])=[N:15][N:14]=1

Participants

5

Reactant 3

HCID 706365-Chloro-2-methylindoleHCID 784901,4-DichlorophthalazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 582471891-chloro-4-(5-chloro-2-methyl-1H-indol-3-yl)phthalazineYield 87.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

5-Chloro-2-methylindole (0.74 g, 2.26 mmol) and 1,4-dichloro-phthalazine (0.45 g, 2.26 mmol) were treated with 30 mL of 1,2-dichloroethane and 3.2=mol of AlCl3 (427 mg). The resulting suspension was heated to 65° C. overnight. The reaction was cooled and quenched with 3 mL water. The resultant precipitate was filtered and dried under vacuum to give 0.65 g of the sub-title compound. MS: ESI (negative): 326, 328 (M−H).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 3 mL water
  3. filtrationThe resultant precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-140d3b308563424381de2693e14b7d2e
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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