1,2-Dichloroethane → 2-Methoxy-4-methylbenzamide

HRID 1686123Notes

Reaction equation

HRID 1686123 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].C(Cl)CCl.C1C=CC2N(O)N=[N:23]C=2C=1.N>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([NH2:23])=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 5971642-Methoxy-4-methylbenzoic acid

Product 1

HCID 219473972-Methoxy-4-methylbenzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-methoxy-4-methylbenzoic acid (20 g, 120.4 mmol), EDC (23.1 g, 120.4 mmol) and HOBt (16.3 g, 120.4 mmol) in dichloromethane (1 L) was added NH3 (7N in MeOH, 52 mL, 3 eq) dropwise. The reaction mixture was stirred at room temperature overnight then washed successively with HCl (1N), saturated aq. NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane to give 16.5 gr of 2-methoxy-4-methylbenzamide (83% yield).

Workup

  1. washthen washed successively with HCl (1N), saturated aq. NaHCO3, water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c22e5e1e9f094375bc9092380c2981b9
Source dataset
uspto-grants-2012_04
Patent number
US08148536B2

Reaction notes

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