Water → HCID 19348363, compound

HRID 1637253Notes

Reaction equation

HRID 1637253 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]2[CH2:17][CH2:18][C:19](O)=[O:20].[C:22](OC(=O)C)(=[O:24])C.O>C(O)=O>[CH:22]([N:9]1[C:10]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]3[C:19](=[O:20])[CH2:18][CH2:17][CH:7]([C:6]=23)[CH:8]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 19348146HCID 19348146, compound

Product 1

HCID 19348363HCID 19348363, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

7-methyl-2-phenyl-2,3-dihydroindole-3-propionic acid (13.47 g) synthesized as in Example 1, steps 1 and 2 was dissolved in formic acid (50 ml) and to the solution was added acetic anhydride (4.53 ml) under cooling with ice. The mixture was stirred for 3 days at room temperature. After adding water, the reaction mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from an ether/hexane mixed solvent to yield 13.07 g (97%) of the titled compound as pale brown crystals.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was crystallized from an ether/hexane mixed solvent

Sources & evidence

ORD record
ord-5c6354b921fc4d93b45db104cee0e0db
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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