Aluminum(III) Chloride → HCID 59641676, compound

HRID 1867866Notes

Reaction equation

C([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[N:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:10]1[C:11]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[CH:12][C:13](=[O:14])[NH:8][N:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-benzyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridazin-3(2H)-one (6.4 g, 15.7 mmol) in toluene (100 mL) at 90° C. was added aluminum chloride (5.23 g, 39.3 mmol) in one portion. After addition, the reaction mixture was stirred at 90° C. for 20 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to reduce the volume to about 50 mL, then water (150 mL) was added. The resulting mixture was sonicated for 5 min, then stirred at room temperature for 10 min. The resulting suspension was filtered, the collected solid was washed with water (20 mL×3), hexanes (20 mL×3) and dried in a 50° C. vacuum oven for 16 h to afford 4.2 g (76%) of the title compound as a white solid. HPLC/MS (method A): retention time=3.27 min, (M+H)+=317.0. 1H NMR (CDCl3, 400 MHz): δ 11.6 (S, 1H), 7.17-7.40 (m, 6H), 6.90-7,10 (m, 3H).

Workup

additionAfter addition
temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
additionwater (150 mL) was added
customThe resulting mixture was sonicated for 5 min
stirringstirred at room temperature for 10 min
filtrationThe resulting suspension was filtered
washthe collected solid was washed with water (20 mL×3), hexanes (20 mL×3)
customdried in a 50° C. vacuum oven for 16 h

Sources & evidence

ORD record: ord-80fd5958f043484b95af9d7f40f35d8f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632837B2

Reaction notes

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