Ammonia → 3-Methoxy-2-methylbenzamide

HRID 1760723Notes

Reaction equation

HRID 1760723 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].C1C=CC2N(O)N=[N:19]C=2C=1.N>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:19])=[O:7]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 70214833-Methoxy-2-MethylBenzoic Acid

Product 1

HCID 160946953-Methoxy-2-methylbenzamideYield 58.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-2-methylbenzoic acid (5.0 g, 30 mmol) in CH2Cl2 (90 ml) and DMF (90 ml) was treated with HOBt (4.06 g, 30 mmol) and WSCDI (5.75 g, 30 mmol) and the resulting mixture stirred at RT for 20 min. After cooling to 0° C. ammonia (2H in EtOH, 30 ml, 60 mmol) was added and the mixture stirred for a further 2 h. The mixture was filtered, the solvent was removed from the filtrate. The crude material was taken up in CH2Cl2 and washed with water and brine and dried (Na2SO4), which gave a white solid (2.9 g) on isolation.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for a further 2 h
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed from the filtrate
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4), which

Sources & evidence

ORD record
ord-dbac52c2bb1b4c1ea2e25c87c21c6b30
Source dataset
uspto-grants-2005_01
Patent number
US06844362B2

Reaction notes

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