Acetic Anhydride → N-{6-phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-yl}-acetamide

HRID 252447Notes

Reaction equation

HRID 252447 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([NH2:18])[C:12]([CH:19]([CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH2:20][CH2:21][CH:22]=[CH2:23])=[CH:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>S(=O)(=O)(O)O.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([NH:18][C:30](=[O:32])[CH3:31])[C:12]([CH:19]([CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH2:20][CH2:21][CH:22]=[CH2:23])=[CH:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 672683566-Phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-ylamine

Product 1

HCID 67268795N-{6-phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-yl}-acetamide

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the solid isolated in Step D (5.08 g, 17.6 mmol) in acetic anhydride (20 mL), sulfuric acid (1 drop) was added. The reaction mixture was stirred at room temperature for four hours. The reaction mixture was then concentrated to yield a residue. The residue was dissolved in ethyl acetate (300 mL). The resulting solution was extracted with sodium hydroxide (1.0 N) solution twice, hydrochloric acid (1.0 N) once, and brine once, and then was dried over magnesium sulfate. The solution was filtered and concentrated to yield N-{6-phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-yl}-acetamide as a yellow solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customto yield a residue
  3. extractionThe resulting solution was extracted with sodium hydroxide (1.0 N) solution twice
  4. dry with materialhydrochloric acid (1.0 N) once, and brine once, and then was dried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1af0dd7bbd4f45b8b02c548010ded33d
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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