p-Anisoyl chloride → HCID 67165918, compound

HRID 553012Notes

Reaction equation

HRID 553012 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([OH:13])=[O:12])[CH2:3][CH2:2]1.[C:14](Cl)(=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]([C:11]([OH:13])=[O:12])[CH2:3][CH2:2]2)=[O:23])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 139310671,2,3,4-Tetrahydroquinoline-4-carboxylic acid

Product 1

HCID 67165918HCID 67165918, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2,3,4-Tetrahydro-quinoline-4-carboxylic acid (305 mg, 1.89 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL). Anisoyl chloride (644 mg, 3.78 mmol) was added followed by diisopropylethylamine (733 mg, 1.01 mL, 15.67 mmol). The reaction was stirred at room temperature for 7 days. The mixture was concentrated and partitioned between chloroform and sodium hydroxide (1 M, aqueous). The chloroform extract was set aside. The aqueous phase was acidified with concentrated hydrochloric acid (pH=3-4). The aqueous phase was then extracted with ethyl acetate (three times). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was used without further purification. MS m/z: 312 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between chloroform and sodium hydroxide (1 M, aqueous)
  3. extractionThe chloroform extract
  4. extractionThe aqueous phase was then extracted with ethyl acetate (three times)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-54813765b992474bbdfb40b73c57ab4e
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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