Sodium Hydroxide → HCID 20134508, compound

HRID 1995409Notes

Reaction equation

Cl.N[C:3]1[C:17]([Cl:18])=[CH:16][C:6]([CH:7]([O:14][CH3:15])[CH2:8][NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][C:4]=1[Cl:19].N([O-])=O.[Na+].[OH-].[Na+]>[PH2](O)=O.O>[ClH:18].[C:10]([NH:9][CH2:8][CH:7]([O:14][CH3:15])[C:6]1[CH:16]=[C:17]([Cl:18])[CH:3]=[C:4]([Cl:19])[CH:5]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture containing 6.55 g of 4-amino-N-tert-butyl-3,5-dichloro-β-methoxyphenethylamine hydrochloride in 66 ml of 50% hypophosphorous acid is cooled to 5° C. and 1.52 g of NaNO2 in 15 ml of H2O is added dropwise. Rapid foaming occurs from gas evolution and after 0.5 hours at 5° C., the mixture is stirred further at room temperature for two hours. It is then made alkaline with 50% aqueous NaOH solution, and the mixture is kept at below 25° C. with addition of ice. The mixture is extracted with 3×100 ml of CH2Cl2 and the combined organic phases are washed with 200 ml of brine, dried (MgSO4), and evaporated to dryness in vacuo to give 5.1 g of the title compound in the form of the free base. This product is dissolved in 50 ml of EtOH and acidified at 5° with 4 4N HCl to afford a light orange precipitate, which is collected. This gives 3.36 g, mp 278°-280° dec, of the title compound which is recrystallized from isopropanol to give 2.35 g, mp 280° C. dec.

Workup

additionthe mixture is kept at below 25° C. with addition of ice
extractionThe mixture is extracted with 3×100 ml of CH2Cl2
washthe combined organic phases are washed with 200 ml of brine
dry with materialdried (MgSO4)
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-3fe119bc3bc2439f89f8674b91ac865e
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04404222

Reaction notes

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