Methanol → HCID 22025351, compound

HRID 1792835Notes

Reaction equation

HRID 1792835 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([NH2:10])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].CO>ClCCl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([NH:10][C:19](=[O:21])[CH3:20])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22025336HCID 22025336, compound

Product 1

HCID 22025351HCID 22025351, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-2-methoxy-5,6-dimethyl-phenylamine (4.9 g, 26 mmol) is dissolved in dichloromethane (20 mL) and pyridine (8 mL) and cooled to 0° C. Acetic anhydride (3.7 mL, 39 mmol) and DMAP (85 mg, 0.7 mmol) are added and the reaction is allowed to warm to room temperature. After stirring 2 h, the reaction is diluted with EtOAc (500 mL) and washed with water, 2N HCl (2×50 mL), water, brine and dried over MgSO4 and concentrated. The crude reaction mixture is dissolved in dichloromethane and a minimal amount of MeOH and then added to a dry pad of silica gel. The product is eluted with 50 to 80% EtOAc/hexanes to provide N-(3-chloro-2-methoxy-5,6-dimethyl-phenyl)-acetamide.

Workup

  1. washwashed with water, 2N HCl (2×50 mL), water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude reaction mixture
  5. washThe product is eluted with 50 to 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-c9c0277dacc746b3a8d39d989cf54fd1
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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