Hydrochloric Acid → HCID 22749253, compound

HRID 1414513Notes

Reaction equation

HRID 1414513 reaction equation
[C:1]([CH2:6][C:7]([N:9]([CH3:21])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[N+:18]([O-])=O)=[O:8])([O:3][CH2:4][CH3:5])=[O:2].C(O)C.[BH4-].[Na+].Cl>[Pd](Cl)Cl.O>[C:1]([CH2:6][C:7]([N:9]([CH3:21])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[NH2:18])=[O:8])([O:3][CH2:4][CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 53920515HCID 53920515, compound

Product 1

HCID 22749253HCID 22749253, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

5 g of N-carbethoxy acetyl N-methyl 4-methoxy 2-nitro aniline are dissolved in 50 c.c. of hot ethanol. After cooling, 15 c.c. of water and 3 c.c. of a 2% solution of palladium chloride are added. Then 5 c.c. of a 20% aqueous solution of sodium borohydride are introduced, while cooling. This is agitated for thirty minutes, without allowing the temperature to exceed 40° C. Then, the excess of reagent is decomposed by acidifying to pH = 2 with hydrochloric acid. After cessation of the gaseous emission, the medium is filtered then neutralised with addition of ammonium hydroxide, N-carbethoxy acetyl N-methyl 4-methoxy o-phenylene diamine precipitates. The precipitate is filtered, washed with water, filtered with suction and dried. Thus, there are obtained 3.75 g of N-carbethoxy acetyl N-methyl 4-methoxy o-phenylene diamine, which is purified by recrystallization in ethanol.

Workup

  1. temperatureAfter cooling
  2. temperaturewhile cooling
  3. customto exceed 40° C
  4. filtrationAfter cessation of the gaseous emission, the medium is filtered
  5. additionthen neutralised with addition of ammonium hydroxide, N-carbethoxy acetyl N-methyl 4-methoxy o-phenylene diamine
  6. customprecipitates
  7. filtrationThe precipitate is filtered
  8. washwashed with water
  9. filtrationfiltered with suction
  10. customdried

Sources & evidence

ORD record
ord-b6d52664edd948da82aea09f8e9d919b
Source dataset
uspto-grants-1977_01
Patent number
US04001408

Reaction notes

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