2-chloro-N-(2-nitrophenyl)acetamide → HCID 8084295, compound

HRID 1415653Notes

Reaction equation

HRID 1415653 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:14])[CH2:12]Cl)([O-:3])=[O:2].[CH3:15][C@H:16]1[O:21][C@@H:20]([CH3:22])[CH2:19][NH:18][CH2:17]1>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:14])[CH2:12][N:18]1[CH2:17][C@@H:16]([CH3:15])[O:21][C@@H:20]([CH3:22])[CH2:19]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 2224432-chloro-N-(2-nitrophenyl)acetamideHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 8084295HCID 8084295, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2-nitrophenyl)-2-chloroacetamide (8.6 g), 2,6-cis-dimethylmorpholine (9.2 g) and ethanol (100 ml) was heated together under reflux for 3 hours. The ethanol was evaporated off and the residue treated with water (100 ml). The resultant suspension was filtered and the solid recrystallised from ethanol to give N-(2-nitrophenyl)-2-(2,6-cis-dimethylmorpholino)acetamide (8.5 g), m.p. 127°-129° C. (with decomposition) which was then dissolved in methanol (100 ml). Platinum oxide (0.3 g) was added to the solution which was then shaken in an atmosphere of hydrogen at atmospheric pressure and laboratory temperature until 1.9 litres of hydrogen had been absorbed. The mixture was filtered and the ethanol evaporated off to give a white solid which was recrystallised from water to give N-(2-aminophenyl)-2-(2,6-cis-dimethylmorpholino)acetamide (5.4 g), m.p. 104°-106° C. (with decomposition).

Workup

  1. temperaturewas heated together
  2. temperatureunder reflux for 3 hours
  3. customThe ethanol was evaporated off
  4. additionthe residue treated with water (100 ml)
  5. filtrationThe resultant suspension was filtered
  6. customthe solid recrystallised from ethanol

Sources & evidence

ORD record
ord-065c85abc1f341b9903439a73b2bbd8a
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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