Tetrahydrofuran → N-[3-(4-aminophenoxy)phenyl]-3-(1-cyanocyclopropyl)benzamide

HRID 2190398Notes

Reaction equation

HRID 2190398 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].O1CCCC1>[C].[Pd].CO>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:28]=[CH:29][CH:30]=[C:6]([C:3]4([C:1]#[N:2])[CH2:5][CH2:4]4)[CH:7]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 673112323-(1-cyanocyclopropyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide

Product 1

HCID 67312701N-[3-(4-aminophenoxy)phenyl]-3-(1-cyanocyclopropyl)benzamideYield 111.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Using 3-(1-cyanocyclopropyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide (5.1 g, 12.7 mmol), tetrahydrofuran (50 mL), methanol (50 mL) and 10% palladium-carbon (455.9 mg) as starting materials, and in the same manner as in Example A12(iii), the title compound (5.25 g) was obtained as a colorless amorphous substance. The obtained compound was used in the next reaction without a further purification.

Sources & evidence

ORD record
ord-e3444e1de7a74ec9af6574d0685ac5df
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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