Ammonia → Hydrochloric Acid

HRID 1890484Notes

Reaction equation

HRID 1890484 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[C:5]([F:11])[C:4]=1[N+:12]([O-])=O.O.N.[ClH:17]>C(O)(=O)C.CCOCC.[Zn].C(OCC)(=O)C>[F:11][C:5]1[C:6]([F:10])=[C:7]([F:9])[CH:8]=[C:3]([NH:2][CH3:1])[C:4]=1[NH2:12].[ClH:17]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 713000963,4,5-Trifluoro-N-methyl-2-nitrobenzenamine

Product 2

HCID 313Hydrochloric AcidHCID 86762004HCID 86762004, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of methyl(3,4,5-trifluoro-2-nitrophenyl)amine (0.5 g) in acetic acid (7.5 ml) is treated portionwise with zinc powder (793 mg). The reaction medium is stirred at ambient temperature (20° C.) until complete reduction. Water (13 ml) and 28% ammonia are added to pH 7, and then the reaction medium is depleted using ethyl acetate (3×50). The organic extracts are combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oil obtained is taken up in ether (50 ml) and then 2N HCl is added thereto. The solid formed is filtered off. 3,4,5-Trifluoro-N1-methylbenzene-1,2-diamine is isolated in its hydrochloride form (508 mg), and is used in the next stage.

Workup

  1. dry with materialdried over magnesium sulphate
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe oil obtained
  5. customThe solid formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-179b571865224c29a6b734a7ce70ba58
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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