4-Methylmorpholine → 2-Amino-6-methoxybenzamide

HRID 591713노트

반응식

HRID 591713 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[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]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:15])=[O:5]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353572-Amino-6-methoxybenzoic Acid

생성물 1

HCID 122648142-Amino-6-methoxybenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-amino-6-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) was added. The mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was extracted with ethylacetate (4×100 mL), the combined organic phase was washed with water and brine, and dried over anhydrous sodium sulfate; the solvent was evaporated to give 2-amino-6-methoxy-benzamide as an off-white solid. Yield: 1.90 g, (65%).

후처리

  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 ethylacetate (4×100 mL)
  4. washthe combined organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-5433fdcfe75c4111bad2426fabcc7433
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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