Pyridine → HCID 19348338, compound

HRID 1637252Notes

Reaction equation

HRID 1637252 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]2[CH2:18][CH2:19][C:20](O)=[O:21].N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(Cl)Cl>[C:29]([N:8]1[C:9]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]3[C:20](=[O:21])[CH2:19][CH2:18][CH:6]([C:5]=23)[CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19348274HCID 19348274, compound

Product 1

HCID 19348338HCID 19348338, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-methoxy-2-phenyl-2,3-dihydroindole-3-propionic acid (10.2 g) synthesized as in Example 1, steps 1 and 2, was dissolved in anhydrous methylene chloride (80 ml). Pyridine (2.77 ml), then acetic anhydride (3.24 ml) were added to the solution under cooling with ice, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into ice water. The organic layer of the mixture was separated, washed with 1N hydrochloric acid, water and saturated aqueous solution of sodium chloride successively and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to yield 11.5 g (99%) of the titled compound as a crude rubber-like product.

Workup

  1. temperatureunder cooling with ice
  2. customThe organic layer of the mixture was separated
  3. washwashed with 1N hydrochloric acid, water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0f10f4c9d1f84138b9ee288cba38f9e9
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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