N-methyl-2-pyrrolidone → HCID 71255169, compound

HRID 540349Notes

Reaction equation

HRID 540349 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[O:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][NH:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>[Cl-].[Na+].O>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:17]2[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:14][CH2:15][CH2:16]2)[CH:11]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 6075032,4-DichloroquinolineHCID 222379922,3,4,5-Tetrahydro-1,4-benzoxazepine--hydrogen chloride (1/1)

Product 1

HCID 71255169HCID 71255169, compoundYield 382.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 2,4-dichloroquinoline (198 mg, 0.1 mmol), 2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (186 mg, 0.1 mmol), diisopropylethylamine (0.4 mL) and 5 mL of N-methyl-2-pyrrolidone was heated with stirring at 100° C. overnight. The mixture was cooled to room temperature, diluted with brine, and extracted with ethyl acetate (30 mL×3). The organic layers were combined and washed with brine. The solvent was dried over sodium sulfate and removed under reduced pressure to give a residue which was purified by column chromatography on silica gel to give 119 mg of product as a white solid. MS obsd. (ESI+) [(M+H)+] 311.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washwashed with brine
  5. dry with materialThe solvent was dried over sodium sulfate
  6. customremoved under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d256a962496346149260e7c70a86e158
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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