Ammonia → HCID 18442918, compound

HRID 458728Notes

Reaction equation

HRID 458728 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)=[CH:12][CH:11]=1)[C:6]([OH:8])=O)=[O:4].S(Cl)(Cl)=O.[NH3:34]>C1C=CC=CC=1.C(OCC)(=O)C>[C:6]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])(=[O:8])[NH2:34]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 18442905HCID 18442905, compound

Product 1

HCID 18442918HCID 18442918, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(methoxycarbonyl)-3-[4-[2-(6-quinolinoxy)ethoxy]phenyl]propionic acid (2.11 g, 5.29 mmol) in benzene (20 ml) at room temperature is added thionyl chloride (0.76 g, 6.34 mmol). Then the mixture was heated at 80° C. for 90 min. After cooled to room temperature, the solvent is removed under a vacuum. To the residue is added 28% ammonia solution (5.49 ml, 79.30 mmol) at room temperature. The mixture is stirred for 30 min, dissolved in ethyl acetate (20 ml), washed with brine (3×15 ml), dried over sodium sulfate, and concentrated. The crude product is crystallized from ethanol to give title compound (1.20 g, 57%). HRMS calcd for C22H26N2O5: 398.4558. Found: 398.4554. MA calcd for C22H26N2O5: C, 66.32%; H, 6.58%; N, 7.03%. Found: C, 66.44%; H, 6.54%; N, 7.05%

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe solvent is removed under a vacuum
  3. washwashed with brine (3×15 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is crystallized from ethanol

Sources & evidence

ORD record
ord-2051fec963c8434a80b7ae5eb5b72ad6
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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