Methanol → HCID 68505396, compound

HRID 1808336Notes

Reaction equation

HRID 1808336 reaction equation
S(Cl)(Cl)=O.[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([OH:18])=[O:17])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[CH3:19]O>>[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 39733728HCID 39733728, compound

Product 1

HCID 68505396HCID 68505396, compound

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (13 g; 1.5 equiv.) was added dropwise at 0° C., in the course of 5-10 minutes, to a solution of crude 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetic acid (stage 5; 14 g; 1 equiv.) in 140 ml of methanol, and the resulting reaction mixture was then heated for 6 hours at reflux (70° C.). When the conversion was complete, the reaction solution was concentrated under reduced pressure and the residue was taken up in 150 ml of water, rendered basic (pH 7-8) with sodium carbonate and finally extracted with 2×150 ml of chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10-12% ethyl acetate/-hexane). Methyl 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetate (4 g) was obtained in the form of a colorless oil.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas then heated for 6 hours
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. extractionfinally extracted with 2×150 ml of chloroform
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, 10-12% ethyl acetate/-hexane)

Sources & evidence

ORD record
ord-9e34484fea0f45db8bcc923e6f984592
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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