Ammonia → 2-Amino-3-methoxybenzamide

HRID 591749Notes

Reaction equation

HRID 591749 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:15]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.N>C1COCC1.O>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2557202-Amino-3-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 185365712-Amino-3-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-3-methoxy benzoic acid (5.00 g, 29.9 mmol) in THF (50 mL) were added EDCl (6.88 g, 35.9 mmol), HOBt (4.85 g, 35.9 mmol), N-methylmorpholine (3.60 g, 35.9 mmol), and aqueous ammonia (50% v/v, 30 mL). Then, the reaction mixture was stirred at room temperature for 48 hours. Then, water was added and the product was extracted with ethyl acetate (2×250 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous Na2SO4. Removal of solvent gave product 2-amino-3-methoxy-benzamide as a light orange solid. Yield: 1.70 g (34%).

Workup

  1. extractionthe product was extracted with ethyl acetate (2×250 mL)
  2. washThe combined organic phase was washed with water
  3. dry with materialbrine, and dried over anhydrous Na2SO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-83f039f79786465c8f7945b0617fcf87
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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