Potassium Hydroxide → HCID 86736860, compound

HRID 1701360Notes

Reaction equation

HRID 1701360 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[N:16][OH:17])[CH2:11][O:12][CH2:13][CH2:14][CH3:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[Cl:19][CH2:20][CH2:21][NH2:22].[OH-].[K+]>CN(C)C=O>[ClH:19].[NH2:22][CH2:21][CH2:20][O:17][N:16]=[C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:11][O:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 97937372-Chloroethylamine hydrochlorideHCID 71395346N-[1-(4-Nitrophenyl)-2-propoxyethylidene]hydroxylamine

Product 1

HCID 86736860HCID 86736860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

10 Mmol of 4'-nitro-2-propoxyacetophenone oxime, 10.4 mmol of 2-chloroethyl amine hydrochloride and 1.4 g of powdered potassium hydroxide were added to 25 ml of dimethyl formamide while stirring at 10° C. After stirring for two days at room temperature the dimethyl formamide was evaporated in vacuo, the residue was brought in water and then 2 N hydrochloric acid was added until pH 3. The remaining oxime was removed by means of ether, after which 30 ml of 2 N sodium hydroxide solution were added. Then three extractions with ether were carried out. The collected ether layers were washed twice with a 5% sodium bicarbonate solution and then dried on sodium sulphate. After removing the ether in vacuo the residue was dissolved in absolute ethanol and converted into the little compound by means of alcoholic hydrochloric acid. After recrystallization from alcohol/ether the melting point was 128°-130° C.

Workup

  1. customwas evaporated in vacuo
  2. addition2 N hydrochloric acid was added until pH 3
  3. customThe remaining oxime was removed by means of ether
  4. additionafter which 30 ml of 2 N sodium hydroxide solution were added
  5. extractionThen three extractions with ether
  6. washThe collected ether layers were washed twice with a 5% sodium bicarbonate solution
  7. customdried on sodium sulphate
  8. customAfter removing the ether in vacuo the residue
  9. dissolutionwas dissolved in absolute ethanol
  10. customAfter recrystallization from alcohol/ether the melting point was 128°-130° C.

Sources & evidence

ORD record
ord-0fd0e0be020b455e98820bd6ee30fbe6
Source dataset
uspto-grants-1980_03
Patent number
US04192893

Reaction notes

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