Hydrochloric Acid → 3'-Amino-4'-methoxyacetanilide

HRID 894415

Reaction equation

HRID 894415 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11](OC(=O)C)(=[O:13])[CH3:12].Cl>O>[CH3:12][C:11]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([NH2:1])[CH:7]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 119762,4-Diaminoanisole

Product 1

HCID 807793'-Amino-4'-methoxyacetanilideYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Other aqueous processes of acylation have been taught to yield the single desired isomer compound I where R is --CH3 and --XR1 is --COCH3, but at lower yield. German 1,543,625, Example 1, teaches the acylation of freshly-distilled 2,4-diaminoanisole with acetic anhydride in water solution, without the addition of hydrochloric acid, to give 3-amino-4-methoxyacetanilide in 75% yield before recrystallization. Publication, Board of Federal Intelligence Agency, P.B. 74 051, p. 33 teaches a similar conversion of 2,4-diaminoanisole to 2-amino-4-acetamidoanisole, in aqueous solution, with acetic anhydride, in the presence of magnesia at 65% yield.

Workup

  1. customat lower yield

Sources & evidence

ORD record
ord-8d2cfeabcbce45d1ba862323d484a9ef
Source dataset
uspto-grants-1981_08
Patent number
US04283556

Linked notes

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