Ammonia → 2-Amino-5-methoxybenzamide

HRID 591756Notes

Reaction equation

HRID 591756 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C[N:15](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.N>C1COCC1.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2779305-Methoxyanthranilic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 203382172-Amino-5-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-amino-5-methoxy-benzoic acid (5.00 g, 30.0 mmol) in THF (50 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.50 g, 39.0 mmol), 1-hydroxybenzotriazole (4.50 g, 33.0 mmol) and 4-methylmorpholine (3.6 mL, 33.0 mmol) and the reaction mixture was stirred at room temperature for 1 hours. Then, 50% aqueous NH3 (8 mL, 105.0 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. Water (100 mL) was added and the product was extracted with ethyl acetate. Solvent was evaporated in vacuo and the residue was washed with ether to give 2-amino-5-methoxy-benzamide as a white solid. Yield: 2.62 g (53%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. extractionthe product was extracted with ethyl acetate
  3. customSolvent was evaporated in vacuo
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-1b58eaa91583411786e6cc89fe325758
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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