Benzoyl chloride → 2-Oxo-1-propylindolin-3-yl benzoate

HRID 1523038Notes

Reaction equation

HRID 1523038 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH3:13])[C:3]1=[O:14].C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C.ClCCl>[C:22]([O:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH3:13])[C:3]1=[O:14])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 904179583-Hydroxy-1-propylindolin-2-one

Product 1

HCID 904164392-Oxo-1-propylindolin-3-yl benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flame dried flask cooled under argon was added the crude 3-hydroxy-1-propylindolin-2-one (0.1 grams, 0.52 mmol) and DMAP (0.007 grams, 0.057 mmol). This was taken up in 5.0 mL of dichloromethane. While stirring at room temperature triethyl amine (78 μL, 0.57 mmol) was added followed by benzoyl chloride (67 μL, 0.57 mmol). The reaction stirred at room temperature until all of the starting material had been consumed. Once complete, the reaction was diluted with water, and the two layers separated. The aqueous layer was washed with dichloromethane twice. The combined organic solution was dried with sodium sulfate, filtered, and concentrated. Chromatography on silica gel using Hexanes/Ethyl acetate (8:2) afforded the desired compound. Yield, 67% for the two steps. 1H-NMR δ 8.11 (d, 2H), 7.58 (dd, 1H), 7.44 (m, 3H), 7.36 (t, 1H), 7.05 (t, 1H), 6.89 (d, 1H), 6.19 (s, 1H), 3.72 (m, 2H), 1.77 (m, 2H), 1.03 (t, 3H).

Workup

  1. customTo a flame dried flask
  2. temperaturecooled under argon
  3. additionwas added
  4. customhad been consumed
  5. additionOnce complete, the reaction was diluted with water
  6. customthe two layers separated
  7. washThe aqueous layer was washed with dichloromethane twice
  8. dry with materialThe combined organic solution was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-627b976cc2234211a24df8c07edd14d0
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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