Pyridine → HCID 85699589, compound

HRID 1655950Notes

Reaction equation

HRID 1655950 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5](=[CH:11][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl>[C:24]([NH:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 237992diethyl 4-aminobenzene-1,2-dicarboxylate

Product 1

HCID 85699589HCID 85699589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diethyl 4-aminophthalate (660 mg) in methylene chloride (40 mL) at 0° was treated with pyridine (0.25 mL) and acetyl chloride (0.22 mL). The reaction mixture was allowed to warm to 23° and stirred for 16 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and methylene chloride. The organic layer was washed with water, 2N hydrochloric acid and brine, dried (MgSO4) and evaporated. The residue was dissolved in ethyl acetate, which upon standing afforded the title compound as white crystals (350 mg). M.p. 118°-121°.

Workup

  1. temperatureto warm to 23°
  2. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate and methylene chloride
  3. washThe organic layer was washed with water, 2N hydrochloric acid and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in ethyl acetate

Sources & evidence

ORD record
ord-c2aed1bf84a74fec8fa6b278da926f8c
Source dataset
uspto-grants-1993_10
Patent number
US05252560

Reaction notes

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