Hydrochloric Acid → HCID 86672697, compound

HRID 2168487Notes

Reaction equation

HRID 2168487 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:7]1.Cl>C1COCC1>[O:2]=[CH:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66899269HCID 66899269, compound

Product 1

HCID 86672697HCID 86672697, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1-(3,3-dimethoxypropyl)-1H-indole-7-carboxylate (1.6 g, 5.8 mmol) from Step A above, 2 N HCl (15 mL) and THF (15 mL) were heated at reflux for 4 h. The reaction was quenched with solid sodium bicarbonate and adjusted to pH 8 and the aqueous phase was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate) to give methyl 1-(3-oxopropyl)-1H-indole-7-carboxylate (278 mg, 21%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 9.77 (s, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.18 (d, J=3.0 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 6.57 (d, J=3.0 Hz, 1H), 4.72 (t, J=6.5 Hz, 2H), 3.96 (s, 3H), 2.99 (t, J=6.5 Hz, 2H).

Workup

  1. temperatureat reflux for 4 h
  2. customThe reaction was quenched with solid sodium bicarbonate
  3. extractionthe aqueous phase was extracted with ethyl acetate (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography (silica gel, 80:20 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-97aa9d4513df4936b41ee760075f52ff
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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