Sodium Carbonate → 4-Pyrrolidin-1-ylcarbonylmethyl-o-phenylenediamine

HRID 35589Notes

Reaction equation

HRID 35589 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[N+:15]([C:18]1[CH:24]=[C:23]([CH2:25][C:26]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:27])[CH:22]=[CH:21][C:19]=1[NH2:20])([O-])=O>O.CO>[N:28]1([C:26]([CH2:25][C:23]2[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([NH2:15])[CH:24]=2)=[O:27])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 212945102-Nitro-4-pyrrolidin-1-ylcarbonylmethylaniline

Product 1

HCID 212945704-Pyrrolidin-1-ylcarbonylmethyl-o-phenylenediamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of sodium dithionite (245 g) and sodium carbonate (196 g) in water (1129 ml) and methanol (1029 ml) was stirred and 2-nitro-4-pyrrolidin-1-ylcarbonylmethylaniline (30.5 g) was added over a period of five minutes. A further portion of water (1468 ml) was added and the solution was heated under reflux for 65 minutes. The volume was reduced in vacuo in several stages with any solid material removed by filtration between each stage. Any solid so removed was washed with methanol and the washings combined with the final filtrate. The resulting solution was evaporated to dryness and the residue dried by azeotropic distillation with toluene and then ethanol. The dried residue was extracted with boiling ethanol and the solution filtered to give a solution which yielded 4-pyrrolidin-1-ylcarbonylmethyl-o-phenylenediamine (m.p. 105°-108° C.) on evaporation.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 65 minutes
  3. customremoved by filtration between each stage
  4. customAny solid so removed
  5. washwas washed with methanol
  6. customThe resulting solution was evaporated to dryness
  7. dry with materialthe residue dried by azeotropic distillation with toluene
  8. extractionThe dried residue was extracted with boiling ethanol
  9. filtrationthe solution filtered
  10. customto give a solution which

Sources & evidence

ORD record
ord-cf09a46b23fe4fe7bfdeac2ad78d3f9c
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

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