Benzonitrile, 2-(3,4-dichlorophenoxy)- → HCID 19926666, compound

HRID 1612795Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].C(=O)([O-])O.[Na+]>C(OCC)C>[ClH:11].[Cl:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 10 g of anhydrous aluminum chloride in 150 ml of dry diethyl ether was added dropwise under nitrogen to a suspension of 3.1 g of lithium aluminum hydride in 150 ml of dry diethyl ether, and the mixture was cooled at 0° C. After 30 min at 0° C., a solution of 5.0 g of 2-(3,4-dichlorophenoxy)benzonitrile in 150 ml of dry diethyl ether was added slowly. The mixture was stirred for 24 h at 25° C., and a concentrated aqueous solution of sodium hydrogen carbonate was added. The precipitate was filtered off, the filtrate was evaporated to dryness, dissolved in ethyl acetate, and acidified with a concentrated solution of hydrochloric acid in ethanol. The precipitate was collected and recrystallized from a mixture of ethanol and diethyl ether, to give in 75% yield 2-(3,4-dichlorophenoxy)benzenemethanamine hydrochloride. mp 213° C.

Workup

filtrationThe precipitate was filtered off
customthe filtrate was evaporated to dryness
dissolutiondissolved in ethyl acetate
customThe precipitate was collected
customrecrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record: ord-56d8f63501e34337863efb1030ad59e9
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190965

Reaction notes

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