Pyridine → Ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate

HRID 2418375Notes

Reaction equation

HRID 2418375 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].N1C=CC=CC=1>C(Cl)Cl>[C:1]([NH:5][C:6]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 20446209Ethyl 2-(2-amino-3-phenoxyphenyl)acetate

Product 1

HCID 20446298Ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetyl chloride (1.38 g.) in methylene chloride (10 ml.) was added to a mixture of ethyl 2-(2-amino-3-phenoxyphenyl)acetate (4.3 g.), pyridine (1.9 g.) and dried methylene chloride (50 ml.) over 10 minutes at 5° C. with stirring and stirred for 30 minutes at the same temperature. The reaction mixture was concentrated under reduced pressure and to the residue was added 10% hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was washed with water, dried over magnesium sulfate and then evaporated. The residue was crystallized with a mixture of benzene and n-hexane to give the captioned compound (3.65 g.). mp 106° to 107° C.

Workup

  1. stirringstirred for 30 minutes at the same temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  3. additionwas added 10% hydrochloric acid
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was crystallized with a mixture of benzene and n-hexane
  9. customto give the captioned compound (3.65 g.)

Sources & evidence

ORD record
ord-d740174023344918927dd7aaae7d8074
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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