Ammonium Chloride → HCID 53417591, compound

HRID 514257Notes

Reaction equation

HRID 514257 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([N+:17]([O-])=O)=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:14][C:12]1[C:11]([NH2:17])=[CH:10][C:3]([C:4]([NH:6][CH:7]2[CH2:9][CH2:8]2)=[O:5])=[C:2]([Cl:1])[CH:13]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86713980HCID 86713980, compound

Product 1

HCID 53417591HCID 53417591, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-N-cyclopropyl-4,5-dinitrobenzamide (7.5 g, 26.3 mmol) was initially charged in ethanol (200 ml) and water (40 ml). At room temperature, ammonium chloride (2.53 g, 47.4 mmol) was added and the reaction mixture was heated to 60° C. At this temperature, iron powder (14.7 g, 263 mmol) was added in portions and the reaction mixture was then heated under reflux for 4 h. The ethanol was removed under reduced pressure and the remaining aqueous suspension was filtered through Celite. The filtrate was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulphate. After removing the solvent under reduced pressure, 4 g (68% of theory) of 4,5-diamino-2-chloro-N-cyclopropylbenzamide were obtained. 1H NMR (D6-DMSO): δ 0.44-0.48 (m, 2H), 0.61-0.64 (m, 2H), 2.71-2.75 (m, 1H), 4.68 (bs, 2H), 4.98 (bs, 2H), 6.47 (s, 1H), 6.55 (s, 1H), 7.95-7.97 (d, 1H).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureunder reflux for 4 h
  3. customThe ethanol was removed under reduced pressure
  4. filtrationthe remaining aqueous suspension was filtered through Celite
  5. extractionThe filtrate was extracted three times with ethyl acetate
  6. washthe combined organic phases were washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customAfter removing the solvent under reduced pressure

Sources & evidence

ORD record
ord-e3d0b305c07a4b4a9b438fb31b99c9ed
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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