Hydrochloric Acid → HCID 18358864, compound

HRID 428443Notes

Reaction equation

Cl.[C:2]1([C:8]2[C:12]([C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[N+:21]([O-])=O)=[C:11]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.B#[Ni]>[C:2]1([C:8]2[C:12]([C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[NH2:21])=[C:11]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:10][N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of nickel boride (3.56 g) ard 1 N HCl (16 mL) in methanol (65 mL) was added to ethyl 3-phenyl-4-(4-chloro-2-nitrobenzoyl)-1H-pyrazole-5-carboxylate (1.5 g, 3.7 mmol) and the mixture heated to 60° C. for 18 hours. The reaction mixture was filtered and the filtrate concentrated via rotovap to a green solid (2.38 g). The solid was dissolved in ethyl acetate (100 mL) and extracted with water (2×50 mL) and brine (1×50 mL). The organic layer was dried over sodium sulfate and concentrated to a dark green oil (1.5 g) which was washed with a small amount of hexanes to yield the title compound as a yellow solid (0.855 g, 62%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated via rotovap to a green solid (2.38 g)
dissolutionThe solid was dissolved in ethyl acetate (100 mL)
extractionextracted with water (2×50 mL) and brine (1×50 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated to a dark green oil (1.5 g) which
washwas washed with a small amount of hexanes

Sources & evidence

ORD record: ord-35ca251f89634920ae6d00041fce1261
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313290B1

Reaction notes

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