4-Methylmorpholine → 2-Amino-4-methoxybenzamide

HRID 591724Notes

Reaction equation

HRID 591724 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[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.[NH4+].[OH-]>C1COCC1>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 3510102-Amino-4-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 140230022-Amino-4-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-4-methoxy-benzoic acid (3.00 g, 17.9 mmol) in THF (90 mL), EDCl (7.89 g, 41.1 mmol) and HOBt (7.95 g, 51.9 mmol) were added and stirred at room temperature for 30 minutes. Then, N-methylmorpholine (6.15 g, 60.0 mmol) and aqueous 50% (v/v) NH4OH (12 mL, 171.4 mmol) were added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (4×100 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous sodium sulfate. Solvent was evaporated to give 2-amino-4-methoxy-benzamide as an off-white solid. Yield: 1.80 g, (60%).

Workup

  1. stirringThe mixture was stirred for 16 hours at room temperature
  2. customThe solvent was removed under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate (4×100 mL)
  4. washThe combined organic phase was washed with water
  5. dry with materialbrine, and dried over anhydrous sodium sulfate
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-0b7fdd842aa14799a40de6ba58265e20
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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