Formic Acid → 2-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)aminonitrobenzene

HRID 2291437Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([NH:15][CH2:16][CH2:17][OH:18])[CH:3]=1.C(O)=O>C(N(CC)CC)C.[Pd]>[OH:11][CH2:10][CH2:9][NH:8][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([NH:15][CH2:16][CH2:17][OH:18])[C:5]=1[N+:12]([O-:14])=[O:13]

Participants

Conditions

Temperature: 70 °C

Procedure

354 mg of palladium at a concentration of 10% on charcoal is added to 0.084 mole (23.1 g) of 4-chloro-2-(β-hydroxyethyl)amino-6-(β-hydroxyethyl)aminonitrobenzene in 23.7 g of triethylamine. 7 ml of formic acid are then run in dropwise. A high exothermicity is noted. The reaction mixture is heated to 70° C. for 1 hour 30. After dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration. The filtrate, evaporated to dryness under reduced pressure, enables a dry extract to be obtained. After dilution of the dry extract with water, the expected product precipitates. After being filtered off, washed with water and then dried under vacuum in the presence of phosphorus pentoxide, it is recrystallized twice from isopropanol. It melts at 103°-104° C., resolidifies and then melts at 112°-113° C.

Workup

customAfter dilution of the reaction mixture with ethanol, the catalyst is removed by hot filtration
customThe filtrate, evaporated to dryness under reduced pressure
extractionextract
customto be obtained
extractionAfter dilution of the dry extract with water
customthe expected product precipitates
filtrationAfter being filtered off
washwashed with water
dry with materialdried under vacuum in the presence of phosphorus pentoxide, it
customis recrystallized twice from isopropanol

Sources & evidence

ORD record: ord-a5be459db66240a1964eda0f5f408658
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797129

Reaction notes

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