Pyridine → Methyl 2-(acetylamino)-4-(4-morpholinyl)benzoate

HRID 884452Notes

Reaction equation

HRID 884452 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:11][C:2]=1[NH:1][C:18](=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58805162HCID 58805162, compound

Product 1

HCID 58805166Methyl 2-(acetylamino)-4-(4-morpholinyl)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 2-amino-4-morpholin-4-ylbenzoate (55 mg; 0.23 mmol) in dry CH2Cl2 (2 mL) was added acetic anhydride (0.05 mL; 0.53 mmol) and pyridine (0.02 mL; 0.25 mmol) via syringe at room temperature under a nitrogen atmosphere. The resulting solution was allowed to stir for 22 hours, then diluted with EtOAc (15 mL) and washed with 0.5 N aqueous hydrochloric acid, water, and brine, then dried (MgSO4), filtered and concentrated in vacuo to provide the amide as a white solid (56 mg; 88%).

Workup

  1. washwashed with 0.5 N aqueous hydrochloric acid, water, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45f48a8bd68a47f4a2cad1019c9db1c1
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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