Hydrochloric Acid → HCID 17860739, compound

HRID 1353146Notes

Reaction equation

HRID 1353146 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][CH:14]=[C:15]2[CH2:20][CH2:21][C:22]([OH:24])=[O:23].Cl>O>[OH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][CH:14]=[C:15]2[CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 17860756HCID 17860756, compound

Product 1

HCID 17860739HCID 17860739, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

To pyridine hydrochloride (200 g), 3-(5-methoxy-3,4-dihydronaphthalen-1-yl)propanoic acid (25.1 g; known compound (see J. Chem. Soc. Perkin Trans. I., 1739–1742(1987)) was added, followed by stirring at 180° C. for 3 hours. The reaction mixture was cooled to room temperature, and diluted with water. The aqueous layer was acidified with a concentrated hydrochloric acid. The aqueous layer was extracted with an ethyl acetate. The extract was extracted with a saturated aqueous sodium hydrogen carbonate solution. The combined aqueous layer was acidified with a concentrated hydrochloric acid, followed by extracting with an ethyl acetate. The combined organic layer was washed with a saturated saline, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain the title compound (11.8 g) having the following physical data.

Workup

  1. additionknown compound (see J. Chem. Soc. Perkin Trans. I., 1739–1742(1987)) was added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe aqueous layer was extracted with an ethyl acetate
  4. extractionThe extract was extracted with a saturated aqueous sodium hydrogen carbonate solution
  5. extractionby extracting with an ethyl acetate
  6. washThe combined organic layer was washed with a saturated saline
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbc8a4b374e34ad2a2c7227fe4e6c813
Source dataset
uspto-grants-2007_05
Patent number
US07220864B2

Reaction notes

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