Acetic Acid → Hydrochloric Acid

HRID 1890483Notes

Reaction equation

HRID 1890483 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5](CN)=[C:4]([N+:11]([O-])=O)[CH:3]=1.O.[NH3:15].[ClH:16].[C:17](O)(=O)C>CCOCC.[Zn].C(OCC)(=O)C>[Cl:16][C:6]1[CH:5]=[C:4]([NH2:11])[C:3]([NH:15][CH3:17])=[CH:2][C:7]=1[Cl:8].[ClH:1]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 86762003HCID 86762003, compound

Product 2

HCID 313Hydrochloric AcidHCID 30163614,5-Dichloro-2-(methylamino)aniline

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (4,5-dichloro-2-nitrophenyl)methylamine (500 mg) in acetic acid (7.5 ml) is treated portionwise with zinc powder (740 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. 4,5-Dichloro-N-methylbenzene-1,2-diamine is isolated in its hydrochloride form (510 mg), and is used in the next state.

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-2cd6ad61e32741778dbab9ee17783480
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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